Cyclopenta[a]naphthaline derivatives

ABSTRACT

The present invention relates to cyclopenta[a]naphthalene derivatives of the general formulae I to V 
                         
in which B, Z, A, n, R, X 1 , X 1a , X 1b , X 2 , X 3 , E 1  and E 2  are as defined in the claims, to the use thereof in liquid-crystalline media, to liquid-crystalline media comprising at least one of these cyclopenta[a]naphthalene derivatives, and to electro-optical display elements containing these liquid-crystalline media.

The present invention relates to cyclopenta[a]naphthalene derivatives,to liquid-crystalline media comprising these derivatives, and toelectro-optical display elements containing these liquid-crystallinemedia. In particular, the invention relates to cyclopenta[a]naphthalenederivatives of negative dielectric anisotropy.

Liquid crystals have found widespread use since the first commerciallyusable liquid-crystalline compounds were found about 30 years ago. Knownareas of application are, in particular, displays for watches and pocketcalculators, and large display panels as used in railway stations,airports and sports arenas. Further areas of application are displays ofportable computers and navigation systems and video applications. Forthe last-mentioned applications in particular, high demands are made ofthe response times and contrast of the images.

The spatial arrangement of the molecules in a liquid crystal has theeffect that many of its properties are direction-dependent. Ofparticular importance for use in liquid-crystal displays are theoptical, dielectric and elastomechanical anisotropies. Depending onwhether the molecules are oriented with their longitudinal axesperpendicular or parallel to the two plates of a capacitor, the latterhas a different capacitance; in other words, the dielectric constant εof the liquid-crystalline medium has different values for the twoorientations. Substances whose dielectric constant is greater when thelongitudinal axes of the molecules are oriented perpendicular to thecapacitor plates than when they are oriented parallel are referred to asdielectrically positive. In other words, if the dielectric constantε_(∥) parallel to the longitudinal axes of the molecules is greater thanthe dielectric constant ε_(⊥) perpendicular to the longitudinal axes ofthe molecules, the dielectric anisotropy Δε=ε_(∥)ε_(⊥) is greater thanzero. Most liquid crystals used in conventional displays fall into thisgroup.

Both the polarisability of the molecule and the permanent dipole momentplay a role for the dielectric anisotropy. On application of a voltageto the display, the longitudinal axis of the molecules orients itself insuch a way that the larger of the dielectric constants becomeseffective. The strength of the interaction with the electric fielddepends on the difference between the two constants. In the case ofsmall differences, higher switching voltages are necessary than in thecase of large differences. The introduction of suitable polar groups,such as, for example, nitrile groups or fluorine, into theliquid-crystal molecules enables a broad range of working voltages to beachieved.

In the case of the liquid-crystalline molecules used in conventionalliquid-crystal displays, the dipole moment oriented along thelongitudinal axis of the molecules is larger than the dipole momentoriented perpendicular to the longitudinal axis of the molecules. Theorientation of the larger dipole moment along the longitudinal axis ofthe molecule also determines the orientation of the molecule in aliquid-crystal display in the field-free state. In the most widespreadTN (“twisted nematic”) cells, a liquid-crystalline layer with athickness of only from about 5 to 10 μm is arranged between twoplane-parallel glass plates, onto each of which an electricallyconductive, transparent layer of tin oxide or indium tin oxide (ITO) hasbeen vapour-deposited as electrode. A likewise transparent alignmentlayer, usually consisting of a plastic (for example polyimides), islocated between these films and the liquid-crystalline layer. Thisalignment layer serves to bring the longitudinal axes of the adjacentliquid-crystalline molecules into a preferential direction throughsurface forces in such a way that, in the voltage-free state, they lieuniformly on the inside of the display surface with the same alignmentin a flat manner or with the same small tilt angle. Two polarisationfilms which only enable linear-polarised light to enter and escape areadhesively bonded to the outside of the display in a certainarrangement.

By means of liquid crystals in which the larger dipole moment isoriented parallel to the longitudinal axis of the molecule, veryhigh-performance displays have already been developed. In most caseshere, mixtures of from 5 to 20 components are used in order to achieve asufficiently broad temperature range of the mesophase and short responsetimes and low threshold voltages. However, difficulties are still causedby the strong viewing-angle dependence in liquid-crystal displays as areused, for example, for laptops. The best imaging quality can be achievedif the surface of the display is perpendicular to the viewing directionof the observer. If the display is tilted relative to the observationdirection, the imaging quality deteriorates drastically under certaincircumstances. For greater comfort, attempts are being made to maximisethe angle through which the display can be tilted from the viewingdirection of an observer without significantly reducing the imagingquality. Attempts have recently been made to improve the viewing-angledependence using liquid-crystalline compounds whose dipole momentperpendicular to the longitudinal axis of the molecules is larger thanthat parallel to the longitudinal axis of the molecule. The dielectricanisotropy Δε is negative. In the field-free state, these molecules areoriented perpendicular to the glass surface of the display. By achievinga plurality of domains, it has been possible to achieve an improvementin the viewing-angle dependence using liquid-crystalline media ofnegative dielectric anisotropy. This technology can also be used toachieve shorter response times in displays and better contrast values.Displays of this type are known as VA-TFT (“vertically aligned”)displays.

DE 44 34 975 A1 discloses tricyclic compounds of the general formula

in which the symbols and indices are defined as follows:

R¹ is —F, —CN, —Cl, —CF₃ or has, independently of R², one of themeanings mentioned for R²;

R² is H or a straight-chain or branched alkyl radical having from 1 to20 carbon atoms (with or without an asymmetrical carbon atom), in which,in addition, one or more —CH₂— groups (but not those bonded directly tothe five-membered ring) may be replaced by —O—, —S—, —CH═CH—, —C≡C—,cyclo-propane-1,2-diyl, —Si(CH₃)₂—, 1,4-phenylene, 1,4-cyclohexylene,1,3-cyclo-pentylene, 1,3-cyclobutylene or 1,3-dioxane-2,5-diyl, with theproviso that oxygen atoms and sulfur atoms must not be bonded directly,and in which, in addition, one or more H atoms of the alkyl radical maybe substituted by F, Cl, Br or OR³ (where R³═H or straight-chainC₁-C₆-alkyl), or an optically active or racemic group;

Ring B is

A¹ is 1,4-phenylene, 1,4-cyclohexylene, pyridine-2,5-diyl,pyrimidine-2,5-diyl, 1,3,4-thiadiazole-2,5-diyl, 1,3-thiazole-2,5-diyl,1,3-thiazole-2,4-diyl, in which, in addition, one or more hydrogens maybe substituted by F;

M¹ is a single bond, —C≡C—, —CH₂CH₂—, —O—CO—, —CO—O—, —CO—, —OCH₂—,—CH₂O— or —O—CO—O—; and m is zero or one.

US Patent Application US 2003/0108684 A1 furthermore discloses tricycliccompounds of the general formula

in which the symbols and indices are defined as follows:

R¹ is H, F, CF₃, OCF₃, OCF₂H, OCFH₂, an alkyl radical or an alkoxyradical or an alkenyl radical or an alkenyloxy radical; R² is H or analkyl radical or an alkoxy radical or an alkenyl radical or analkenyloxy ad; M¹ is —C(═O)O—, —OC(═O)—, —CH₂O—, —OCH₂—, —OCF₂—, —CF₂O—,—C≡C—, —CH₂CH₂—, —CF₂CF₂—, —CF═CFC(═O)O— or a single bond; M² is—C(═O)O—, —OC(═O)—, —CH₂O—, —OCH₂—, —CH₂CH₂—, —CF₂CF₂— or a single bond;A¹ and A² are phenylene-1,4-diyl or cyclohexane-1,4-diyl, each of whichis unsubstituted or mono- or disubstituted by F, or cyclohexene-1,4-diylor 1,3-dioxane-2,5-diyl, each of which is unsubstituted ormonosubstituted by F; m and n are 0 or 1, where m+n=0 or 1; L¹, L², L³,L⁴ and L⁵ are, independently of one another, H or F, where at least oneof L¹, L², L³, L⁴ and L⁵ is F, L¹, L² and L³ are H if L⁵ is F, and L⁴and L⁵ are H if L³ is F. The five-membered ring fused to the naphthalenestructure has (with the exception of two intermediates containing acyclopentanone ring which are formed in the synthesis of theabove-mentioned compounds) no further substituents apart from the-(-M²-A²-)_(n)-R² radical and also contains no further endocyclic doublebonds.

However, the dielectric anisotropy Δε of the compounds disclosed inthese two documents is not sufficient to ensure satisfactory properties,in particular sufficiently low characteristic voltages, for example inVA-TFT displays.

Development in the area of liquid-crystalline materials is far fromcomplete. In order to improve the properties of liquid-crystallinedisplay elements, attempts are constantly being made to develop novelcompounds which enable such displays to be optimised.

An object of the present invention is therefore to provide compoundshaving advantageous properties for use in liquid-crystalline media. Theyshould preferably have negative dielectric anisotropy, which makes themparticularly suitable for use in liquid-crystalline media for VAdisplays.

This object is achieved in accordance with the invention by acyclopenta-[a]naphthalene derivative of one of the general formulae I,II, III, IV and V

-   -   A is in each case, independently of one another, 1,4-phenylene,        in which ═CH— may be replaced once or twice by ═N—, and which        may be monosubstituted to tetrasubstituted, independently of one        another, by halogen (—F, —Cl, —Br —I), —CN, —CH₃, —CH₂F, —CHF₂,        —CF₃, —OCH₃, —OCH₂F, —OCHF₂ or —OCF₃, 1,4-cyclohexylene,        1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH₂—        may in each case be replaced once or twice, independently of one        another, by —O— or —S— in such a way that heteroatoms are not        linked directly, and which all may be monosubstituted or        poly-substituted by halogen;    -   Z is in each case, independently of one another, a single bond,        a double bond, —CF₂O—, —OCF₂—, —CH₂CH₂—, —CF₂CF₂—, —CF₂—CH₂—,        —CH₂—CF₂—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH₂O—, —OCH₂—, —CF═CH—,        —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—;    -   R is hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical        having from 1 to 15 or 2 to 15 carbon atoms respectively which        is unsubstituted, monosubstituted by —CF₃ or at least        monosubstituted by halogen, where, in addition, one or more CH₂        groups in these radicals may each, independently of one another,        be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a        way that heteroatoms are not linked directly, halogen, —CN,        —SCN, —NCS, —SF₅, —CF₃, —OCF₃, —OCHF₂ or —OCH₂F;    -   X¹, X^(1a), X^(1b), X² and X³ are each, independently of one        another, hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical        having from 1 to 15 or 2 to 15 carbon atoms respectively which        is unsubstituted or at least monosubstituted by halogen, where,        in addition, one or more CH₂ groups in these radicals may each,        independently of one another, be replaced by —O—, —S—, —CO—,        —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not        linked directly, halogen, —CN, —SF₅, —SCN, —NCS, —CF₃, —OCF₃,        —OCHF₂ or —OCH₂F;    -   E¹ and E² are each, independently of one another, hydrogen, an        alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or        2 to 15 carbon atoms respectively which is unsubstituted or at        least mono-substituted by halogen, where, in addition, one or        more CH₂ groups in these radicals may each, independently of one        another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O—        in such a way that heteroatoms are not linked directly, halogen,        —CN, —SCN, —NCS, —SF₅, —CF₃, —OCF₃, —OCHF₂, —OCH₂F or        -(Z-A-)_(n)-R; and    -   n is 0, 1, 2 or 3;        where

in the formula I, ring B does not stand for the formula C if X¹, X² andX³ are simultaneously hydrogen, and

in the formula I, ring B does not stand for the formula e if X² and X³are simultaneously fluorine or if E¹ is hydrogen and simultaneously X¹and X² are fluorine.

Preference is given to cyclopenta[a]naphthalene derivatives of thegeneral formulae I, III and V, and particular preference is given tocyclopenta[a]-naphthalene derivatives of the general formulae I and V.

The compounds all have negative Δε and are therefore suitable, inparticular, for use in VA-TFT displays. The compounds according to theinvention preferably have a Δε of <−2 and particularly preferably a Δεof <−5. The dielectric anisotropy of the compounds according to theinvention enables satisfactorily low characteristic voltages to beachieved, in particular in VA-TFT displays. The compounds exhibit verygood compatibility with the usual substances used in liquid-crystalmixtures for displays.

Furthermore, the compounds of the formulae I to V according to theinvention have values for the optical anisotropy An which areparticularly suitable for use in VA-TFT displays. The compoundsaccording to the invention preferably have a Δn of greater than 0.02 andless than 0.20, particularly preferably less than 0.15.

The other physical, physicochemical or electro-optical parameters of thecompounds according to the invention are also advantageous for use ofthe compounds in liquid-crystalline media. The compounds have, inparticular, a sufficient breadth of the nematic phase and goodlow-temperature and long-term stability as well as sufficiently highclearing points and good viscosities and response times.

It is preferred for at least one of the radicals X¹, X² and X³ orX^(1a), X^(1b), X² and X³ on the naphthalene structure of the formula I,II, III, IV or V to be other than hydrogen.

It is furthermore preferred for ring B to have at least oneelectronegative substituent (—F or ═O). These substituents on ring B areoriented in the same direction, i.e. the same side of the molecule, asthe radicals X¹, X^(1a), X^(1b), X² and X³.

The substituents X¹, X^(1a), X^(1b), X² and X³, preferably CF₃, fluorineand/or chlorine substituents, in particular fluorine substituents, inthe naphthalene structure and the electronegative atoms in ring Bgenerate a dipole moment perpendicular to the longitudinal axis of themolecules, which can, if desired, be further strengthened by suitablesubstituents in the wing units -(Z-A-)_(n)-R. In the field-free state,the compounds of the formulae I to V orient themselves with theirlongitudinal axis of the molecules perpendicular to the treated orcoated glass surface of the display.

particularly preferably the fluorine-substituted rings a, b, f, g and h,in particular ring a.

In the general formulae I to V, A are preferably, independently of oneanother (i.e. if n>1, so that a plurality of identical or differentrings A are present), optionally substituted 1,4-phenylene, optionallysubstituted 1,4-cyclohexylene in which —CH₂— may be replaced once ortwice by —O—, or optionally substituted 1,4-cyclohexenylene.

A are particularly preferably, independently of one another,

A are very particularly preferably 1,4-cyclohexylene rings and/oroptionally mono- or poly-fluorine-substituted 1,4-phenylene rings.

If E¹ and/or E² are -(-Z-A-)_(n)-R, A are preferably 1,4-cyclohexylenerings or optionally fluorine-substituted 1,4-phenylene rings.

Preferred groups Z in the compounds of the general formulae I to V areeach, independently of one another, a single bond, —CF₂O—, —OCF₂—,—CF₂CF₂—, —CH═CH—, —CF═CH—, —CH═CF— or —CF═CF—, particularly preferablya single bond, —CF₂O—, —OCF₂—, —CF₂CF₂—, —CF═CH—, —CH═CF— or —CF═CF—. IfE¹ and/or E² are -(-Z-A-)_(n)-R, Z is in particular in each case asingle bond.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ in the general formulae I to Vmay each, independently of one another, be an alkyl radical—i.e. analiphatic saturated hydrocarbon radical—and/or an alkoxy radical(alkyloxy radical)—i.e. an aliphatic saturated hydrocarbon radicalhaving a terminal O atom—having from 1 to 15 carbon atoms, which isstraight-chain or branched. It is preferably straight-chain, has 1, 2,3, 4, 5, 6 or 7 carbon atoms and accordingly is preferably methyl,ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, propoxy,butoxy, pentoxy, hexoxy or heptoxy.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ may each, independently of oneanother, be oxaalkyl—i.e. one of the non-terminal CH₂ groups in thealkyl radical has been replaced by —O——preferably straight-chain2-oxapropyl (=methoxymethyl), 2-(=ethoxymethyl) or 3-oxabutyl(=methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl or 2-,3-, 4-, 5- or 6-oxaheptyl. Correspondingly, R, E¹, E², X¹, X^(1a),X^(1b), X² and X³ may also, independently of one another, be thioalkylradicals, i.e. alkyl radicals in which a CH₂ group has been replaced by—S—.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ may furthermore each,independently of one another, be an alkenyl radical—i.e. an aliphatichydrocarbon radical containing at least one C═C double bond—having from2 to 15 carbon atoms, which is straight-chain or branched and containsat least one C—C double bond. It is preferably straight-chain and hasfrom 2 to 7 carbon atoms. Accordingly, it is preferably vinyl, prop-1-or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl,hex-1-, -2-, -3-, -4- or -5-enyl, or hept-1-, -2-, -3-, -4-, -5- or-6-enyl. If the two carbon atoms of the C—C double bond are substituted,the alkenyl radical may be in the form of the E- and/or Z-isomer(trans/cis). The respective E-isomers are generally preferred.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ may also, independently of oneanother, be an alkynyl radical having from 2 to 15 carbon atoms, whichis straight-chain or branched and contains at least one C—C triple bond.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ may each, independently of oneanother, be an alkyl radical having from 1 to 15 carbon atoms in whichone CH₂ group has been replaced by —O— and one has been replaced by—CO—, these preferably being adjacent. This thus contains an acyloxygroup —CO—O— or an oxycarbonyl group —O—CO—. This radical is preferablystraight-chain and has from 2 to 6 carbon atoms. Replacement of a CH₂group by —CO— with formation of a keto group is also possible. Thecorresponding radical likewise preferably has from 2 to 6 carbon atoms.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ may each, independently of oneanother, be an alkyl radical having from 1 to 15 carbon atoms in whichone CH₂ group has been replaced by unsubstituted or substituted —CH═CH—and an adjacent CH₂ group has been replaced by CO or CO—O or O—CO, wherethis may be straight-chain or branched. The radical is preferablystraight-chain and has from 4 to 13 carbon atoms.

R, E¹ and E² may each, independently of one another, be an alkyl radicalhaving from 1 to 15 carbon atoms or alkenyl radical having from 2 to 15carbon atoms, each of which is monosubstituted by —CN or —CF₃, thesepreferably being straight-chain. Substitution by —CN or —CF₃ is possiblein any desired position.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ may each, independently of oneanother, be an alkyl radical in which two or more CH₂ groups have beenreplaced by —O— and/or —CO—O—, where this may be straight-chain orbranched. It is preferably branched and has from 3 to 12 carbon atoms.

R, E¹, E², X¹, X^(1a), X^(1b), X² and X³ may each, independently of oneanother, be an alkyl radical or alkoxy radical having from 1 to 15carbon atoms or alkenyl radical having from 2 to 15 carbon atoms, eachof which is at least monosubstituted by halogen, where these radicalsare preferably straight-chain and halogen is preferably —F or —Cl. Inthe case of polysubstitution, halogen is preferably —F. The resultantradicals also include perfluorinated radicals, such as —CF₃ and —OCF₃.In the case of monosubstitution, the fluorine or chlorine substituentcan be in any desired position, but is preferably in the ω-position.

R in the general formulae I to V is particularly preferably an alkylradical, alkoxy radical or alkenyl radical having from 1 to 7 or 2 to 7carbon atoms respectively.

E¹ and E² in the general formulae I to V are preferably, independentlyof one another, hydrogen, an alkyl radical, alkoxy radical or alkenylradical having from 1 to 7 or 2 to 7 carbon atoms respectively, ahalogen or -(-Z-A-)_(n)-R, in which n is 1, Z is a single bond, A is1,4-cyclohexylene or optionally fluorine-substituted 1,4-phenylene, andR is alkyl, alkoxy or alkenyl having from 1 to 7 or 2 to 7 carbon atomsrespectively, particularly preferably hydrogen, an alkyl radical oralkoxy radical having from 1 to 7 carbon atoms, fluorine, chlorine,4-alkyl-substituted 1,4-phenylene or 4-alkyl-substituted1,4-cyclohexylene, and in particular fluorine.

X¹, X^(1a), X^(1b), X² and X³ in the general formulae I to V arepreferably, independently of one another, hydrogen, an alkyl radical,alkoxy radical or alkenyl radical having from 1 to 7 or 2 to 7 carbonatoms respectively which is at least monosubstituted by halogen, or ahalogen. It is particularly preferred here for at least one of X¹, X²and X³ or X^(1a), X^(1b), X² and X³ to be —CF₃, F or Cl. Veryparticularly preferably, all of X¹, X² and X³ or X^(1a), X^(1b), X² andX³ are —CF₃, fluorine or chlorine, and in particular all are fluorine.

Preferred compounds of the general formulae I to V contain a total ofzero, one or two wing units ZA, i.e. n=0, 1 or 2. If a wing group ZA ispresent (n=1), it can be bonded to the cyclopentane ring or to thenaphthalene structure (E¹, E²=-Z-A-R). If n is 2 or 3, the two or threewing groups ZA may be bonded to only one side of the molecule—to thecyclopentane ring or as E¹ or E² to the naphthalene structure—oralternatively to both sides of the molecule—to the cyclopentane ring andas E¹ or E² to the naphthalene structure. n is particularly preferably 0or 1.

In connection with the present invention, halogen is fluorine, chlorine,bromine or iodine.

The compounds of the general formulae I to V are prepared by methodsknown per se, as described in the literature (for example in thestandard works, such as Houben-Weyl, Methoden der organischen Chemie[Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), to beprecise under reaction conditions which are known and suitable for thesaid reactions. Use can be made here of variants which are known per se,but are not mentioned here in greater detail.

If desired, the starting materials can also be formed in situ by notisolating them from the reaction mixture, but instead immediatelyconverting them further into the compounds of the general formulae I toV.

The syntheses of various polysubstituted naphthalene derivatives whichare used to build up the five-membered ring are described by way ofexample in the examples. The starting substances are obtainable bygenerally accessible literature procedures or are commerciallyavailable. The reactions described should likewise be regarded as knownfrom the literature.

An illustrative synthesis for building up the five-membered ring isshown below. The synthesis can be adapted to the particular desiredcompounds of the general formulae I to V through the choice of suitablestarting materials.

Starting from the 4-bromonaphthalene derivative A, reaction with anα,β-unsaturated aldehyde B in the presence of lithium diisopropylamide(LDA) gives compound C. This reacts with palladium catalysis in thepresence of triethylamine with ring closure to give the ketone D(=compound Ie). Starting from the ketone D and 1,3-propanedithiol in thepresence of BF₃/diethyl ether, the corresponding dithiane E is obtained.This is reacted with 1,3-dibromo-5,5-dimethylhydantoin (DBH) and HF inpyridine to give the cyclopenta[a]naphthalene derivative F. Eliminationof HBr in the presence of diazabicycloundecene (DBU) gives thecyclopenta[a]naphthalene derivative G (=compound Ib). Thecyclopenta[a]naphthalene derivative G is hydrogenated on apalladium/carbon catalyst in a hydrogen atmosphere to give thecyclopenta[a]naphthalene derivative H (=compound Ia).

Starting from the ketone D (which, in addition, can also be preparedanalogously to US 2003/0108684 A1, scheme 4), reduction, for exampleusing LiAlH₄, firstly gives access to the alcohol J, from which on theone hand the cyclopenta[a]naphthalene derivative K (=compound Ii) isaccessible by subsequent elimination using acid and on the other handthe cyclopenta[a]naphthalene derivative L (=compound If) is accessibleusing DAST (diaminosulfur trifluoride; cf. M. Hudlicky, OrganicReactions, 35, 1988, 513) analogously to DE 44 34 975 A1.

Starting from the ketone D, the cyclopenta[a]naphthalene derivative M(=compound Ih) is furthermore accessible by reaction with DASTanalogously to the process disclosed in DE 44 34 975 A1.

The reactions described should only be regarded as illustrative. Theperson skilled in the art can carry out corresponding variations of thesyntheses described and also follow other suitable synthetic routes inorder to obtain compounds of the formulae I to V.

As already mentioned, the compounds of the general formulae I to V canbe used in liquid-crystalline media.

The present invention therefore also relates to a liquid-crystallinemedium comprising at least two liquid-crystalline compounds, comprisingat least one compound of the general formulae I to V.

The present invention also relates to liquid-crystalline mediacomprising from 2 to 40, preferably from 4 to 30, components as furtherconstituents besides one or more compounds of the formulae I, II, III,IV and/or V according to the invention. These media particularlypreferably comprise from 7 to 25 components besides one or morecompounds according to the invention. These further constituents arepreferably selected from nematic or nematogenic (monotropic orisotropic) substances, in particular substances from the classes of theazoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl orcyclohexyl benzoates, phenyl or cyclohexyl esters, ofcyclohexanecarboxylic acid, phenyl or cyclohexyl esters ofcyclohexylbenzoic acid, phenyl or cyclohexyl esters ofcyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl esters of benzoicacid, of cyclohexanecarboxylic acid or ofcyclohexylcyclohexanecarboxylic acid, phenylcyclohexanes,cyclohexylbiphenyls, phenylcyclohexylcyclohexanes,cyclohexylcyclohexanes, cyclohexylcyclohexylcyclohexenes,1,4-biscyclohexylbenzenes, 4′,4′-biscyclohexylbiphenyls, phenyl- orcyclohexylpyrimidines, phenyl- or cyclo-hexylpyridines, phenyl- orcyclohexyldioxanes, phenyl- or cyclohexyl-1,3-dithianes,1,2-diphenylethanes, 1,2-dicyclohexylethanes,1-phenyl-2-cyclohexylethanes,1-cyclohexyl-2-(4-phenylcyclohexyl)ethanes,1-cyclohexyl-2-biphenylylethanes, 1-phenyl-2-cyclohexylphenylethanes,optionally halogenated stilbenes, benzyl phenyl ethers, tolans andsubstituted cinnamic acids, as well as corresponding compounds in whichtwo carbocyclic and/or heterocyclic rings or ring systems (for examplecyclohexyls, phenyls, dioxanes, tetrahydropyrans) are linked via adifluorooxymethylene bridge (—CF₂O—). The 1,4-phenylene groups in thesecompounds may also be mono- or polyfluorinated.

The most important compounds suitable as further constituents of mediaaccording to the invention can be characterised by the formulae (VI),(VII), (VIII), (IX) and (X):R′-L-E-R″  (VI)R′-L-COO-E-R″  (VII)R′-L-OOC-E-R″  (VII)R′-L-CH₂CH₂-E-R″  (IX)R′-L—CF₂O-E-R″ (X)

In the formulae (VI), (VII), (VIII), (IX) and (X), L and E, which may beidentical or different, are each, independently of one another, adivalent radical from the group formed by -Phe-, -Cyc-, -Phe-Phe-,-Phe-Cyc-, -Cyc-Cyc-, -Pyr-, -Dio-, -Thp-, -G-Phe- and -G-Cyc- and theirmirror images, where Phe is unsubstituted or fluorine-substituted1,4-phenylene, Cyc is trans-1,4-cyclohexylene or 1,4-cyclohexylene, Pyris pyrimidine-2,5-diyl or pyridine-2,5-diyl, Dio is1,3-dioxane-2,5-diyl, Thp- is tetrahydropyran-2,5-diyl and G is2-(trans-1,4-cyclohexyl)ethyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl or1,3-dioxane-2,5-diyl.

One of the radicals L and E is preferably Cyc or Phe. E is preferablyCyc, Phe or Phe-Cyc. The media according to the invention preferablycomprise one or more components selected from the compounds of theformulae (VI), (VII), (VIII), (IX) and (X) in which L and E are selectedfrom the group consisting of Cyc and Phe and simultaneously one or morecomponents selected from the compounds of the formulae (VI), (VII),(VIII), (IX) and (X) in which one of the radicals L and E is selectedfrom the group consisting of Cyc and Phe and the other radical isselected from the group consisting of -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-,-G-Phe- and -G-Cyc-, and optionally one or more components selected fromthe compounds of the formulae (VI), (VII), (VIII), (IX) and (X) in whichthe radicals L and E are selected from the group consisting of-Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc-.

In a smaller sub-group of the compounds of the formulae (VI), (VII),(VIII), (IX) and (X), R′ and R″ are each, independently of one another,alkyl, alkenyl, alkoxy, alkoxyalkyl (oxaalkyl), alkenyloxy oralkanoyloxy having up to 8 carbon atoms. This smaller sub-group iscalled group A below, and the compounds are referred to by thesub-formulae (VIa), (VIIa), (VIIIa), (IXa) and (Xa). In most of thesecompounds, R′ and R″ are different from one another, one of theseradicals usually being alkyl, alkenyl, alkoxy or alkoxy-alkyl(oxaalkyl).

In another smaller sub-group of the compounds of the formulae (VI),(VII), (VIII), (IX) and (X), which is known as group B, E is

In the compounds of group B, which are referred to by the sub-formulae(VIb), (VIIb), (VIIIb), (IXb) and (Xb), R′ and R″ are as defined for thecompounds of the sub-formulae (VIa) to (Xa) and are preferably alkyl,alkenyl, alkoxy or alkoxyalkyl (oxaalkyl).

In a further smaller sub-group of the compounds of the formulae (VI),(VII), (VIII), (IX) and (X), R″ is —CN. This sub-group is referred tobelow as group C, and the compounds of this sub-group arecorrespondingly described by sub-formulae (VIc), (VIIc), (VIIIc), (IXc)and (Xc). In the compounds of the sub-formulae (VIc), (VIIc), (VIIIc),(IXc) and (Xc), R′ is as defined for the compounds of the sub-formulae(VIa) to (Xa) and is preferably alkyl, alkenyl, alkoxy or alkoxyalkyl(oxaalkyl).

Besides the preferred compounds of groups A, B and C, other compounds ofthe formulae (VI), (VII), (VIII), (IX) and (X) having other variants ofthe proposed substituents are also customary. All these substances areobtainable by methods which are known from the literature or analogouslythereto.

Besides the compounds of the general formulae I, II, III, IV and/or Vaccording to the invention, the media according to the inventionpreferably comprise one or more compounds from groups A, B and/or C. Theproportions by weight of the compounds from these groups in the mediaaccording to the invention are:

-   -   group A: from 0 to 90%, preferably from 20 to 90%, in particular        from 30 to 90%    -   group B: from 0 to 80%, preferably from 10 to 80%, in particular        from 10 to 70%    -   group C: from 0 to 80%, preferably from 5 to 80%, in particular        from 5 to 50%.

The media according to the invention preferably comprise from 1 to 40%,particularly preferably from 5 to 30%, of the compounds of the formulaeI, II, III, IV and/or V according to the invention. Preference isfurthermore given to media comprising more than 40%, in particular from45 to 90%, of compounds of the formulae I, II, III, IV and/or Vaccording to the invention. The media preferably comprise one, two,three, four or five compounds of the formulae I, II, III, IV and/or Vaccording to the invention.

Examples of the compounds of the formulae (VI), (VII), (VIII), (IX) and(X) are the compounds listed below:

where R¹ and R², independently of one another, are —C_(n)H_(2n+1) or—OC_(n)H_(2n+1), and n=1, 2, 3, 4, 5, 6, 7 or 8, and L¹ and L²,independently of one another, are —H or —F,

where m and n, independently of one another, are 1, 2, 3, 4, 5, 6, 7 or8.

The media according to the invention are prepared in a mannerconventional per se. In general, the components are dissolved in oneanother, advantageously at elevated temperature. By means of suitableadditives, the liquid-crystalline phases of the present invention can bemodified in such a way that they can be used in all types ofliquid-crystal display element that have been disclosed hitherto.Additives of this type are known to the person skilled in the art andare described in detail in the literature (H. Kelker/R. Hatz, Handbookof Liquid Crystals, Verlag Chemie, Weinheim, 1980). For example,pleochroic dyes can be used for the preparation of coloured guest-hostsystems or substances can be added in order to modify the dielectricanisotropy, the viscosity and/or the alignment of the nematic phases.

Owing to their negative Δε, the compounds of the formulae I to V areparticularly suitable for use in VA-TFT displays.

The present invention therefore also relates to electro-opticalliquid-crystal display elements containing a liquid-crystalline mediumaccording to the invention.

The invention is explained in greater detail below with reference toworking examples, but without being restricted thereby.

EXAMPLES

The starting substances can be obtained by generally accessibleliterature procedures or are commercially available. The reactionsdescribed are known from the literature.

Example 1

38.8 ml (95.0 mmol) of a 2.5M butyllithium solution in hexane were addedat −75° C. to a solution of 25.0 g (92.0 mmol) of the aromatic compound1 in 200 ml of diethyl ether, and the mixture was stirred for 1 hour.13.4 ml (120 mmol) of formylpiperidine (2) in 15 ml of diethyl etherwere subsequently added at T<−55° C. After a further hour, the batch waswarmed to room temperature, water was added, and the mixture wasacidified. Extraction, drying, evaporation and chromatography on silicagel gave 14.2 g (70%) of the aldehyde 3.

200 ml (100 mmol) of a 0.5M solution of the zinc compound 4 in THF wereadded at −75° C. to a solution of 26.8 g (98.5 mmol) of the aldehyde 3in 100 ml of THF. After 30 minutes, the cooling was removed. Water wasadded to the thawed batch, which was then acidified using 1 N HClsolution and extracted with methyl tert-butyl ether. Drying, evaporationand chromatography on silica gel gave 28.6 g (90%) of the hydroxy ester5.

20.0 g (61.9 mmol) of the hydroxy ester 5 were dissolved in 200 ml oftoluene, 1 g of p-toluenesulfonic acid was added, and the mixture wasrefluxed until the water separation was complete. Evaporation andfiltration through silica gel gave 16.4 g (87%) of the ester 6.

15.0 g (49.2 mmol) of the unsaturated ester 6 were hydrogenated on apalladium catalyst (5%/C) in tetrahydrofuran (THF). Yield: 14.5 g (96%)of the ester 7.

9.0 g (29.3 mmol) of the ester 7 were added at 60° C. to 100 g ofpolyphosphoric acid. The temperature was subsequently increased to 120°C. for 4 hours. After cooling, the batch was added to ice and extractedwith methyl tert-butyl ether. Drying, evaporation and crystallisationgave 4.8 g (63%) of the ketone 8.

5.0 g (19.2 mmol) of the oxo compound 8 were dissolved in 40 ml ofdiethylene glycol dimethyl ether, and 2.3 g (58.5 mmol) of sodiumborohydride were added with ice-cooling. 9 ml of borontrifluoride/diethyl ether complex were subsequently added. After 2 hoursat room temp., the batch was added to sat. sodium hydrogencarbonatesolution. The aqueous phase was extracted with dichloromethane. Drying,evaporation and chromatography on silica gel gave 4.3 g (90%) of thetetrahydronaphthalene 9.

Compounds according to the invention are accessible from compounds 8 and9 or analogous compounds, as is evident to the person skilled in theart, inter alia from the description and the further examples.

Example 2

A solution of 10.6 g (32.7 mmol) of the hydroxy ester 5 was added atroom temp. to a suspension of 40.0 mmol of PCC on 50 g of Celite® in 150ml of dichloromethane. When the reaction was complete (TLC), the batchwas filtered, and the filter cake was washed with methylene chloride.Evaporation and chromatography on silica gel gave 10.1 g (96%) of theoxo ester 10.

The ring closure was carried out as described above for compound 7.Yield: 61 %.

8.6 g (31.1 mmol) of the dione 11 were dissolved in 150 ml of ethanol,and 2.4 g (65.0 mmol) of sodium borohydride were added in portions. Whenthe reaction was complete (TLC), the batch was hydrolysed using water,the ethanol was removed under reduced pressure, and the residue wastaken up in water and extracted with toluene. After evaporation, theproduct 12 was employed in the next step without further purification.

10.0 g of the crude diol 12 were dissolved in 200 ml of toluene, 1 g ofp-toluenesulfonic acid was added, and the mixture was refluxed until thewater separation was complete. Evaporation and filtration through silicagel gave 8.0 g (92%) of the naphthalene 13. Compounds according to theinvention are accessible therefrom (or from analogous compounds), as isevident to the person skilled in the art, inter alia from thedescription and the further examples.

Example 3

30 ml of boron trifluoride/diethyl ether complex were added undernitrogen to a solution of 13.1 g (50.0 mmol) of the ketone 8 and 8.4 ml(100 mmol) of the dithiol in 150 ml of dichloromethane, and the mixturewas stirred overnight. The batch was added slowly to sat. sodiumhydrogencarbonate solution and deacidified. Drying, evaporation andchromatography on silica gel gave 17.2 g (92%) of the protected ketone14.

A solution of 9.3 g (25.0 mmol) of the dithiolane 14 in 60 ml ofdichloromethane was added at −75° C. to a suspension of 30.2 g (105.2mmol) of 1,3-dibromo-5,5-dimethylhydantoin in 60 ml of dichloromethaneand 120 ml of a 65% solution of hydrogen fluoride in pyridine. The batchwas slowly warmed to 0° C. over the course of 3 hours and added to 1500ml of ice-cooled 2N sodium hydroxide solution to which 120 ml of 39%sodium hydrogensulfite solution had been added. The pH was adjusted to8, and the aqueous phase was extracted with methylene chloride. Drying,evaporation and chromatography on silica gel gave 5.2 g (73%) of thefluorinated aromatic compound 15. Compounds according to the inventionare accessible therefrom (or from analogous compounds), as is evident tothe person skilled in the art, inter alia from the description and thefurther examples.

Example 4

The synthesis is carried out in accordance with the reactions describedabove, with the elimination of water from 19 to give 20 likewise beingeffected using p-toluenesulfonic acid. Overall yield: 30%.

Example 5

A solution of 9.0 g (23.6 mmol) of 15 in 50 ml of THF was slowly addedto a suspension of 4.5 g (40.1 mmol) of potassium tert-butoxide in 50 mlof THF, and the mixture was subsequently refluxed overnight. The cooledbatch was diluted with water and extracted with diethyl ether. Drying,evaporation and chromatography on silica gel gave 7.2 g (85%) of thestyrene derivative 22.

Example 6

The reaction was carried out as described above. Yield: 81 %. Compoundsaccording to the invention are accessible from compounds 20, 21 and 22(or analogous compounds), as is evident to the person skilled in theart, inter alia from the description and the following examples.

Example 7

A solution of 13.5 g (60.0 mmol) of the bromofluoronaphthalene 24 in 10ml of THF is added at −75° C. to 27.0 ml of a solution of 2N lithiumdiisopropylamide (LDA) in cyclohexane/ethylbenzene/THF (52.4 mmol) whichhas been diluted with 100 ml of THF. After 2 hours at the lowtemperature, 8.5 g (47.3 mmol) of the aldehyde 23 in 10 ml of THF areadded. After 30 minutes, the cooling is removed, and 100 ml of 1 N HClare added to the batch at 20° C. Extraction of the aqueous phase, dryingof the organic phase, evaporation and chromatography gives the allylalcohol 25.

35.0 g (86.6 mmol) of the allyl alcohol 25, 5.5 g ofbis(tri-o-tolylphosphine)-palladium dichloride and 50 ml oftriethylamine are dissolved in 390 ml of acetonitrile and heated to 90°C. until the allyl alcohol has completely reacted. The cooled batch isintroduced into water. Extraction, drying, evaporation andchromatography gives the ketone 26.

Example 8

10.0 g (30.8 mmol) of the ketone 26 and 3.2 ml (31.0 mmol) ofpropane-dithiol are dissolved in 50 ml of dichloromethane, 7.0 ml ofboron trifluoride/diethyl ether complex are added at from 6 to 7° C.,and the mixture is subsequently stirred overnight at room temperature.The batch is introduced into 10 ml of saturated sodium hydrogencarbonatesolution and stirred until the evolution of gas is complete. Afterextraction of the aqueous phase, drying of the organic phase,evaporation and filtration through silica gel, the resultant residue isemployed in the next step without further purification.

10.0 g of the crude thioketal 27, dissolved in 30 ml of dichloromethane,are added slowly at −75° C. to a mixture of 28.6 g (100 mmol) of1,3-dibromo-5,5-dimethylhydantoin (DBH), 80 ml of a 65% solution ofhydrogen fluoride in pyridine and 50 ml of dichloromethane. The batch issubsequently stirred overnight at room temperature. The reaction mixtureis added to ice-cooled hydrogen sulfite solution and deacidified usingsaturated sodium hydrogencarbonate solution and sodium hydroxidesolution. Extraction, drying, evaporation, re-washing with water,chromatography and crystallisation from hexane gives thecyclopenta[a]naphthalene derivative 28.

6.0 g (14.1 mmol) of the cyclopenta[a]naphthalene derivative 28 aredissolved in 50 ml of dichloromethane, 2.4 ml (16.0 mmol) of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added, and the mixture isstirred at room temperature until the starting material has completelyreacted. The batch is washed with water and saturated sodium chloridesolution, evaporated and chromatographed. The cyclopenta[a]naphthalenederivative 29 is isolated.

Example 9

4.0 g (11.6 mmol) of the cyclopenta[a]naphthalene derivative 29 aredissolved in 50 ml of THF and hydrogenated at room temperature andatmospheric pressure on a palladium catalyst. Evaporation,chromatography on silica gel and crystallisation gives thecyclopenta[a]naphthalene derivative 30.

Example 10

The cyclopenta[a]naphthalene derivative 31 prepared analogously toExamples 7 to 9 was converted into the cyclopenta[a]naphthalenederivative 32 as follows: under nitrogen and at −70° C., 4.5 ml (7.20mmol) of a 15% solution of butyllithium in n-hexane were added to asolution of 2.5 g (7.18 mmol) of the naphthalene derivative 31 in 60 mlof THF. After 1 hour, 0.91 ml (8.0 mmol) of trimethyl borate was addedto the batch. When the addition was complete, the cooling was removed,and the batch was hydrolysed at 10° C. The reaction mixture wasacidified using 2N HCl solution. The aqueous phase was extracted withmethyl tert-butyl ether. The organic phase was washed with sat. NaClsolution, dried over sodium sulfate and evaporated. The residue, whichcontained the boronic acid 32, was employed in the next step withoutfurther purification.

1.3 g (5.0 mmol) of sodium metaborate octahydrate were dissolved in 2.0ml of water under a nitrogen atmosphere, and 83 mg ofbis(triphenylphosphine)palladium(II)chloride, 50 μl of hydraziniumhydroxide and 1.11 g (6.0 mmol) of p-bromoethylbenzene were addedsuccessively. After 5 minutes at room temperature, 2.1 g (6.0 mmol) ofthe boronic acid dissolved in 3.75 ml of THF were added to the batch,and the mixture was heated at the boil overnight. The aqueous phase wasextracted with methyl tert-butyl ether, and the organic phase was washedwith water, dried and evaporated. The purification was carried out bymeans of multiple chromatography on silica gel (heptane).

Example 11

The cyclopenta[a]naphthalene derivative 31 was converted into thecyclopenta[a]naphthalene derivative 35 as follows:

Under nitrogen and at −70° C., 4.5 ml (7.20 mmol) of a 15% solution ofbutyllithium in n-hexane were added to a solution of 2.5 g (7.18 mmol)of the naphthalene derivative 31 in 60 ml of THF. After 1 hour, 1.1 g(8.0 mmol) of 4-propylcyclohexanone in 5 ml of THF were added to thebatch. After 1 hour, the cooling was removed, and the batch washydrolysed at 10° C. The reaction mixture was acidified using 2N HClsolution. The aqueous phase was extracted with methyl tert-butyl ether.The organic phase was washed with sat. NaCl solution, dried over sodiumsulfate and evaporated. The residue was passed through silica gel(methyl tert-butyl ether/heptane 1:10).

A mixture of 50 ml of pyridine and 50 ml of phosphoryl chloride wasadded to a solution of 3.6 g (7.0 mmol) of the benzyl alcohol 34 in 30ml of pyridine at such a rate that the batch boiled. After 4 hours, thebatch was carefully poured into ice/water. The aqueous phase wasextracted with dichloromethane; the organic phase was washed with sat.NaCl solution, dried over sodium sulfate, evaporated and passed throughsilica gel (hexane). 2.0 g (4.0 mmol) of the resultant eliminationproduct were dissolved in 20 ml of THF and hydrogenated on a Pd catalystuntil the uptake of hydrogen was complete. The catalyst was separatedoff, and the solution was evaporated. The residue was passed throughsilica gel (hexane), giving 35 after removal of the solvent.

Example 12

5.0 g (19.2 mmol) of the ketone 8, dissolved in 30 ml of THF, were addedat −70° C. to a mixture of 40 ml of THF, 5.2 ml (41.2 mmol) oftrimethylsilyl chloride and 10.3 ml (20 mmol) of a 2M solution oflithium diisopropylamide. After 30 minutes, 40 ml of triethylamine andsat. sodium hydrogencarbonate solution were added to the batch. Theaqueous phase was extracted with methyl tert-butyl ether. The organicphase was dried over sodium sulfate, evaporated and filtered throughsilica gel (methyl tert-butyl ether/pentane 1:20).

The residue was taken up in 40 ml of THF, and a solution of 4.9 g (20.0mmol) of m-chloroperbenzoic acid in 20 ml of THF was added at 0° C.After 1 hour, water was added to the batch, which was then extractedwith methyl tert-butyl ether. The organic phase was dried over sodiumsulfate, evaporated and filtered through silica gel (methyl tert-butylether/heptane 1:5), giving 4.4 g (80%) of the hydroxy ketone 36.

The synthesis of the thioketal 37 was carried out as already describedin Example 3 for compound 14.

A solution of 14.1 g (40.0 mmol) of the thioketal 37 in 20 ml of THF wasadded to a suspension of 1.8 g (60%, 45.7 mmol) of sodium hydride in 40ml of THF. After 2 hours, 500 mg of tetrabutylammonium iodide and 5.5 ml(45.7 mmol) of benzyl bromide in 20 ml of THF were added to thesuspension. The batch was stirred overnight and subsequently carefullyhydrolysed. The aqueous phase was extracted with methyl tert-butylether. The organic phase was dried over sodium sulfate, evaporated andpassed through silica gel (methyl tert-butyl ether/heptane 1:20), giving16.1 g (91%) of the benzyl ether 38.

The alcohol 39 can be prepared from 38 analogously to the processes ofExamples 7 to 9. During the preparation of the intermediate thioketal,the benzyl ether is cleaved. The protecting group must then bere-introduced in the manner already described.

A mixture of 50 ml of pyridine and 50 ml of phosphoryl chloride wasadded to a solution of 2.9 g (7.0 mmol) of the naphthalene 39 in 30 mlof pyridine at such a rate that the batch boiled. After 4 hours, thebatch was carefully poured onto ice. The aqueous phase was extractedwith dichloromethane, and the organic phase was washed with sat. NaClsolution, dried over sodium sulfate, evaporated and passed throughsilica gel (hexane), giving 1.7 g (62%) of the unsaturated compound 40.

Example 13

The synthesis is carried out in accordance with the procedure indicatedabove in Example 12 for compound 38.

An ethanolic potassium hydroxide solution was added to 7.3 g (17.7 mmol)of the ester 41, and the mixture was refluxed until the reaction wascomplete (TLC). The alcohol was removed in a rotary evaporator. Theresidue was taken up in water and acidified. After extraction withmethyl tert-butyl ether, the organic phase was dried over sodiumsulfate, and the solvent was removed. Thionyl chloride and one drop ofDMF were added to the resultant residue, and the mixture was refluxeduntil the evolution of gas was complete. Excess thionyl chloride wasdistilled off. The crude product 42 was employed in the next stepwithout further purification.

A solution of the acid chloride 42 in 50 ml of dichloromethane was addedslowly at 0° C. to a suspension of 4 g of aluminium chloride in 50 ml ofdichloromethane. When the addition was complete, the reaction wasmonitored by TLC. When the reaction was complete, ice was carefullyadded to the batch. When the evolution of HCl had subsided, the mixturewas diluted with water and acidified. The aqueous phase was extractedwith dichloromethane. The organic phase was washed with sat. sodiumchloride solution, dried over sodium sulfate and evaporated. The residuewas passed through silica gel (methyl tert-butyl ether/heptane 1:5).

11.0 g (30.0 mmol) of the ketone 43 and 4.3 ml (90.0 mmol) ofhydrazinium hydroxide were added to a solution of 6.7 g of potassiumhydroxide in 50 ml of diethylene glycol. The batch was slowly heated to180° C. When the evolution of nitrogen was complete and after cooling toroom temperature, the batch was diluted with water and extracted anumber of times with methyl tert-butyl ether. The organic phase wasdried over sodium sulfate, evaporated and passed through silica gel(methyl tert-butyl ether/heptane 1:20), giving 6.4 g (60%) of the benzylether 44.

The alcohol 45 can be prepared from 44 analogously to the processes ofExamples 7 to 9. During the preparation of the intermediate thioketal,the benzyl ether is cleaved. The protecting group must then bere-introduced in the manner already described.

The synthesis of compound 46 was carried out analogously to the methodindicated in Example 12.

The following compounds are prepared analogously to Examples 1 to 13.“bond” here stands for a single bond:

Examples 14-110

Example E¹ X¹ X² X³ R 14 H H H H CH₃ 15 H H H H C₂H₅ 16 H H H H n-C₃H₇17 H H H H n-C₄H₉ 18 H H H H n-C₅H₁₁ 19 H H H H n-C₆H₁₃ 20 H H H Hn-C₇H₁₅ 21 H H H F CH₃ 22 H H H F C₂H₅ 23 H H H F n-C₃H₇ 24 H H H Fn-C₄H₉ 25 H H H F n-C₅H₁₁ 26 H H H F n-C₆H₁₃ 27 H H H F n-C₇H₁₅ 28 H H FF CH₃ 29 H H F F C₂H₅ 30 H H F F n-C₃H₇ 31 H H F F n-C₄H₉ 32 H H F Fn-C₅H₁₁ 33 H H F F n-C₆H₁₃ 34 H H F F n-C₇H₁₅ 35 H F F F CH₃ 36 H F F FC₂H₅ 37 H F F F n-C₄H₉ 38 H F F F n-C₅H₁₁ 39 H F F F n-C₆H₁₃ 40 H F F Fn-C₇H₁₅ 41 CH₃ H F F CH₃ 42 CH₃ H F F C₂H₅ 43 CH₃ H F F n-C₃H₇ 44 CH₃ HF F n-C₄H₉ 45 CH₃ H F F n-C₅H₁₁ 46 CH₃ H F F n-C₆H₁₃ 47 CH₃ H F Fn-C₇H₁₅ 48 CH₃ F F F CH₃ 49 CH₃ F F F C₂H₅ 50 CH₃ F F F n-C₃H₇ 51 CH₃ FF F n-C₄H₉ 52 CH₃ F F F n-C₅H₁₁ 53 CH₃ F F F n-C₆H₁₃ 54 CH₃ F F Fn-C₇H₁₅ 55 C₂H₅ H F F CH₃ 56 C₂H₅ H F F C₂H₅ 57 C₂H₅ H F F n-C₃H₇ 58C₂H₅ H F F n-C₄H₉ 59 C₂H₅ H F F n-C₅H₁₁ 60 C₂H₅ H F F n-C₆H₁₃ 61 C₂H₅ HF F n-C₇H₁₅ 62 C₂H₅ F F F CH₃ 63 C₂H₅ F F F C₂H₅ 64 C₂H₅ F F F n-C₃H₇ 65C₂H₅ F F F n-C₄H₉ 66 C₂H₅ F F F n-C₅H₁₁ 67 C₂H₅ F F F n-C₆H₁₃ 68 C₂H₅ FF F n-C₇H₁₅ 69 n-C₃H₇ H F F CH₃ 70 n-C₃H₇ H F F C₂H₅ 71 n-C₃H₇ H F Fn-C₃H₇ 72 n-C₃H₇ H F F n-C₄H₉ 73 n-C₃H₇ H F F n-C₅H₁₁ 74 n-C₃H₇ H F Fn-C₆H₁₃ 75 n-C₃H₇ H F F n-C₇H₁₅ 76 n-C₃H₇ F F F CH₃ 77 n-C₃H₇ F F F C₂H₅78 n-C₃H₇ F F F n-C₃H₇ 79 n-C₃H₇ F F F n-C₄H₉ 80 n-C₃H₇ F F F n-C₅H₁₁ 81n-C₃H₇ F F F n-C₆H₁₃ 82 n-C₃H₇ F F F n-C₇H₁₅ 83 n-C₄H₉ H F F CH₃ 84n-C₄H₉ H F F C₂H₅ 85 n-C₄H₉ H F F n-C₃H₇ 86 n-C₄H₉ H F F n-C₄H₉ 87n-C₄H₉ H F F n-C₅H₁₁ 88 n-C₄H₉ H F F n-C₆H₁₃ 89 n-C₄H₉ H F F n-C₇H₁₅ 90n-C₄H₉ F F F CH₃ 91 n-C₄H₉ F F F C₂H₅ 92 n-C₄H₉ F F F n-C₃H₇ 93 n-C₄H₉ FF F n-C₄H₉ 94 n-C₄H₉ F F F n-C₅H₁₁ 95 n-C₄H₉ F F F n-C₆H₁₃ 96 n-C₄H₉ F FF n-C₇H₁₅ 97 n-C₅H₁₁ H F F CH₃ 98 n-C₅H₁₁ H F F C₂H₅ 99 n-C₅H₁₁ H F Fn-C₃H₇ 100 n-C₅H₁₁ H F F n-C₄H₉ 101 n-C₅H₁₁ H F F n-C₅H₁₁ 102 n-C₅H₁₁ HF F n-C₆H₁₃ 103 n-C₅H₁₁ H F F n-C₇H₁₅ 104 n-C₅H₁₁ F F F CH₃ 105 n-C₅H₁₁F F F C₂H₅ 106 n-C₅H₁₁ F F F n-C₃H₇ 107 n-C₅H₁₁ F F F n-C₄H₉ 108 n-C₅H₁₁F F F n-C₅H₁₁ 109 n-C₅H₁₁ F F F n-C₆H₁₃ 110 n-C₅H₁₁ F F F n-C₇H₁₅

Examples 111-228

Example E¹ X¹ X² X³ Z R 111 H H H F Bond CH₃ 112 H H H F Bond C₂H₅ 113 HH H F Bond n-C₄H₉ 114 H H H F Bond n-C₅H₁₁ 115 H H H F Bond n-C₆H₁₃ 116H H H F Bond n-C₇H₁₅ 117 H H F F Bond CH₃ 118 H H F F Bond C₂H₅ 119 H HF F Bond n-C₃H₇ 120 H H F F Bond n-C₄H₉ 121 H H F F Bond n-C₅H₁₁ 122 H HF F Bond n-C₆H₁₃ 123 H H F F Bond n-C₇H₁₅ 124 H F F F Bond CH₃ 125 H F FF Bond C₂H₅ 126 H F F F Bond n-C₃H₇ 127 H F F F Bond n-C₄H₉ 128 H F F FBond n-C₅H₁₁ 129 H F F F Bond n-C₆H₁₃ 130 H F F F Bond n-C₇H₁₅ 131 H F FF CF₂CF₂ CH₃ 132 H F F F CF₂CF₂ C₂H₅ 133 H F F F CF₂CF₂ n-C₃H₇ 134 H F FF CF₂CF₂ n-C₄H₉ 135 H F F F CF₂CF₂ n-C₅H₁₁ 136 H F F F CF₂CF₂ n-C₆H₁₃137 H F F F CF₂CF₂ n-C₇H₁₅ 138 H F F F OCF₂ CH₃ 139 H F F F OCF₂ C₂H₅140 H F F F OCF₂ n-C₃H₇ 141 H F F F OCF₂ n-C₄H₉ 142 H F F F OCF₂ n-C₅H₁₁143 H F F F OCF₂ n-C₆H₁₃ 144 H F F F OCF₂ n-C₇H₁₅ 145 CH₃ H F F Bond CH₃146 CH₃ H F F Bond C₂H₅ 147 CH₃ H F F Bond n-C₃H₇ 148 CH₃ H F F Bondn-C₄H₉ 149 CH₃ H F F Bond n-C₅H₁₁ 150 CH₃ H F F Bond n-C₆H₁₃ 151 CH₃ H FF Bond n-C₇H₁₅ 152 CH₃ F F F Bond CH₃ 153 CH₃ F F F Bond C₂H₅ 154 CH₃ FF F Bond n-C₃H₇ 155 CH₃ F F F Bond n-C₄H₉ 156 CH₃ F F F Bond n-C₅H₁₁ 157CH₃ F F F Bond n-C₆H₁₃ 158 CH₃ F F F Bond n-C₇H₁₅ 159 CH₃ F F F CF₂CF₂CH₃ 160 CH₃ F F F CF₂CF₂ C₂H₅ 161 CH₃ F F F CF₂CF₂ n-C₃H₇ 162 CH₃ F F FCF₂CF₂ n-C₄H₉ 163 CH₃ F F F CF₂CF₂ n-C₅H₁₁ 164 CH₃ F F F CF₂CF₂ n-C₆H₁₃165 CH₃ F F F CF₂CF₂ n-C₇H₁₅ 166 CH₃ F F F OCF₂ CH₃ 167 CH₃ F F F OCF₂C₂H₅ 168 CH₃ F F F OCF₂ n-C₃H₇ 169 CH₃ F F F OCF₂ n-C₄H₉ 170 CH₃ F F FOCF₂ n-C₅H₁₁ 171 CH₃ F F F OCF₂ n-C₆H₁₃ 172 CH₃ F F F OCF₂ n-C₇H₁₅ 173C₂H₅ H F F Bond CH₃ 174 C₂H₅ H F F Bond C₂H₅ 175 C₂H₅ H F F Bond n-C₃H₇176 C₂H₅ H F F Bond n-C₄H₉ 177 C₂H₅ H F F Bond n-C₅H₁₁ 178 C₂H₅ H F FBond n-C₆H₁₃ 179 C₂H₅ H F F Bond n-C₇H₁₅ 180 C₂H₅ F F F Bond CH₃ 181C₂H₅ F F F Bond C₂H₅ 182 C₂H₅ F F F Bond n-C₃H₇ 183 C₂H₅ F F F Bondn-C₄H₉ 184 C₂H₅ F F F Bond n-C₅H₁₁ 185 C₂H₅ F F F Bond n-C₆H₁₃ 186 C₂H₅F F F Bond n-C₇H₁₅ 187 n-C₃H₇ H F F Bond CH₃ 188 n-C₃H₇ H F F Bond C₂H₅189 n-C₃H₇ H F F Bond n-C₃H₇ 190 n-C₃H₇ H F F Bond n-C₄H₉ 191 n-C₃H₇ H FF Bond n-C₅H₁₁ 192 n-C₃H₇ H F F Bond n-C₆H₁₃ 193 n-C₃H₇ H F F Bondn-C₇H₁₅ 194 n-C₃H₇ F F F Bond CH₃ 195 n-C₃H₇ F F F Bond C₂H₅ 196 n-C₃H₇F F F Bond n-C₃H₇ 197 n-C₃H₇ F F F Bond n-C₄H₉ 198 n-C₃H₇ F F F Bondn-C₅H₁₁ 199 n-C₃H₇ F F F Bond n-C₆H₁₃ 200 n-C₃H₇ F F F Bond n-C₇H₁₅ 201n-C₄H₉ H F F Bond CH₃ 202 n-C₄H₉ H F F Bond C₂H₅ 203 n-C₄H₉ H F F Bondn-C₃H₇ 204 n-C₄H₉ H F F Bond n-C₄H₉ 205 n-C₄H₉ H F F Bond n-C₅H₁₁ 206n-C₄H₉ H F F Bond n-C₆H₁₃ 207 n-C₄H₉ H F F Bond n-C₇H₁₅ 208 n-C₄H₉ F F FBond CH₃ 209 n-C₄H₉ F F F Bond C₂H₅ 210 n-C₄H₉ F F F Bond n-C₃H₇ 211n-C₄H₉ F F F Bond n-C₄H₉ 212 n-C₄H₉ F F F Bond n-C₅H₁₁ 213 n-C₄H₉ F F FBond n-C₆H₁₃ 214 n-C₄H₉ F F F Bond n-C₇H₁₅ 215 n-C₅H₁₁ H F F Bond CH₃216 n-C₅H₁₁ H F F Bond C₂H₅ 217 n-C₅H₁₁ H F F Bond n-C₃H₇ 218 n-C₅H₁₁ HF F Bond n-C₄H₉ 219 n-C₅H₁₁ H F F Bond n-C₅H₁₁ 220 n-C₅H₁₁ H F F Bondn-C₆H₁₃ 221 n-C₅H₁₁ H F F Bond n-C₇H₁₅ 222 n-C₅H₁₁ F F F Bond CH₃ 223n-C₅H₁₁ F F F Bond C₂H₅ 224 n-C₅H₁₁ F F F Bond n-C₃H₇ 225 n-C₅H₁₁ F F FBond n-C₄H₉ 226 n-C₅H₁₁ F F F Bond n-C₅H₁₁ 227 n-C₅H₁₁ F F F Bondn-C₆H₁₃ 228 n-C₅H₁₁ F F F Bond n-C₇H₁₅

Examples 229-347

Example E¹ X¹ X² X³ Z R 229 H H H F Bond CH₃ 230 H H H F Bond C₂H₅ 231 HH H F Bond n-C₃H₇ 232 H H H F Bond n-C₄H₉ 233 H H H F Bond n-C₅H₁₁ 234 HH H F Bond n-C₆H₁₃ 235 H H H F Bond n-C₇H₁₅ 236 H H F F Bond CH₃ 237 H HF F Bond C₂H₅ 238 H H F F Bond n-C₃H₇ 239 H H F F Bond n-C₄H₉ 240 H H FF Bond n-C₅H₁₁ 241 H H F F Bond n-C₆H₁₃ 242 H H F F Bond n-C₇H₁₅ 243 H FF F Bond CH₃ 244 H F F F Bond C₂H₅ 245 H F F F Bond n-C₃H₇ 246 H F F FBond n-C₄H₉ 247 H F F F Bond n-C₅H₁₁ 248 H F F F Bond n-C₆H₁₃ 249 H F FF Bond n-C₇H₁₅ 250 H F F F CF₂CF₂ CH₃ 251 H F F F CF₂CF₂ C₂H₅ 252 H F FF CF₂CF₂ n-C₃H₇ 253 H F F F CF₂CF₂ n-C₄H₉ 254 H F F F CF₂CF₂ n-C₅H₁₁ 255H F F F CF₂CF₂ n-C₆H₁₃ 256 H F F F CF₂CF₂ n-C₇H₁₅ 257 H F F F CF₂O CH₃258 H F F F CF₂O C₂H₅ 259 H F F F CF₂O n-C₃H₇ 260 H F F F CF₂O n-C₄H₉261 H F F F CF₂O n-C₅H₁₁ 262 H F F F CF₂O n-C₆H₁₃ 263 H F F F CF₂On-C₇H₁₅ 264 CH₃ H F F Bond CH₃ 265 CH₃ H F F Bond C₂H₅ 266 CH₃ H F FBond n-C₃H₇ 267 CH₃ H F F Bond n-C₄H₉ 268 CH₃ H F F Bond n-C₅H₁₁ 269 CH₃H F F Bond n-C₆H₁₃ 270 CH₃ H F F Bond n-C₇H₁₅ 271 CH₃ F F F Bond CH₃ 272CH₃ F F F Bond C₂H₅ 273 CH₃ F F F Bond n-C₃H₇ 274 CH₃ F F F Bond n-C₄H₉275 CH₃ F F F Bond n-C₅H₁₁ 276 CH₃ F F F Bond n-C₆H₁₃ 277 CH₃ F F F Bondn-C₇H₁₅ 278 CH₃ F F F CF₂CF₂ CH₃ 279 CH₃ F F F CF₂CF₂ C₂H₅ 280 CH₃ F F FCF₂CF₂ n-C₃H₇ 281 CH₃ F F F CF₂CF₂ n-C₄H₉ 282 CH₃ F F F CF₂CF₂ n-C₅H₁₁283 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 284 CH₃ F F F CF₂CF₂ n-C₇H₁₅ 285 CH₃ F F FCF₂O CH₃ 286 CH₃ F F F CF₂O C₂H₅ 287 CH₃ F F F CF₂O n-C₃H₇ 288 CH₃ F F FCF₂O n-C₄H₉ 289 CH₃ F F F CF₂O n-C₅H₁₁ 290 CH₃ F F F CF₂O n-C₆H₁₃ 291CH₃ F F F CF₂O n-C₇H₁₅ 292 C₂H₅ H F F Bond CH₃ 293 C₂H₅ H F F Bond C₂H₅294 C₂H₅ H F F Bond n-C₃H₇ 295 C₂H₅ H F F Bond n-C₄H₉ 296 C₂H₅ H F FBond n-C₅H₁₁ 297 C₂H₅ H F F Bond n-C₆H₁₃ 298 C₂H₅ H F F Bond n-C₇H₁₅ 299C₂H₅ F F F Bond CH₃ 300 C₂H₅ F F F Bond C₂H₅ 301 C₂H₅ F F F Bond n-C₃H₇302 C₂H₅ F F F Bond n-C₄H₉ 303 C₂H₅ F F F Bond n-C₅H₁₁ 304 C₂H₅ F F FBond n-C₆H₁₃ 305 C₂H₅ F F F Bond n-C₇H₁₅ 306 n-C₃H₇ H F F Bond CH₃ 307n-C₃H₇ H F F Bond C₂H₅ 308 n-C₃H₇ H F F Bond n-C₃H₇ 309 n-C₃H₇ H F FBond n-C₄H₉ 310 n-C₃H₇ H F F Bond n-C₅H₁₁ 311 n-C₃H₇ H F F Bond n-C₆H₁₃312 n-C₃H₇ H F F Bond n-C₇H₁₅ 313 n-C₃H₇ F F F Bond CH₃ 314 n-C₃H₇ F F FBond C₂H₅ 315 n-C₃H₇ F F F Bond n-C₃H₇ 316 n-C₃H₇ F F F Bond n-C₄H₉ 317n-C₃H₇ F F F Bond n-C₅H₁₁ 318 n-C₃H₇ F F F Bond n-C₆H₁₃ 319 n-C₃H₇ F F FBond n-C₇H₁₅ 320 n-C₄H₉ H F F Bond CH₃ 321 n-C₄H₉ H F F Bond C₂H₅ 322n-C₄H₉ H F F Bond n-C₃H₇ 323 n-C₄H₉ H F F Bond n-C₄H₉ 324 n-C₄H₉ H F FBond n-C₅H₁₁ 325 n-C₄H₉ H F F Bond n-C₆H₁₃ 326 n-C₄H₉ H F F Bond n-C₇H₁₅327 n-C₄H₉ F F F Bond CH₃ 328 n-C₄H₉ F F F Bond C₂H₅ 329 n-C₄H₉ F F FBond n-C₃H₇ 330 n-C₄H₉ F F F Bond n-C₄H₉ 331 n-C₄H₉ F F F Bond n-C₅H₁₁332 n-C₄H₉ F F F Bond n-C₆H₁₃ 333 n-C₄H₉ F F F Bond n-C₇H₁₅ 334 n-C₅H₁₁H F F Bond CH₃ 335 n-C₅H₁₁ H F F Bond C₂H₅ 336 n-C₅H₁₁ H F F Bond n-C₃H₇337 n-C₅H₁₁ H F F Bond n-C₄H₉ 338 n-C₅H₁₁ H F F Bond n-C₅H₁₁ 339 n-C₅H₁₁H F F Bond n-C₆H₁₃ 340 n-C₅H₁₁ H F F Bond n-C₇H₁₅ 341 n-C₅H₁₁ F F F BondCH₃ 342 n-C₅H₁₁ F F F Bond C₂H₅ 343 n-C₅H₁₁ F F F Bond n-C₃H₇ 344n-C₅H₁₁ F F F Bond n-C₄H₉ 345 n-C₅H₁₁ F F F Bond n-C₅H₁₁ 346 n-C₅H₁₁ F FF Bond n-C₆H₁₃ 347 n-C₅H₁₁ F F F Bond n-C₇H₁₅

Examples 348-466

Example E¹ X¹ X² X³ Z R 348 H H H F Bond CH₃ 349 H H H F Bond C₂H₅ 350 HH H F Bond n-C₃H₇ 351 H H H F Bond n-C₄H₉ 352 H H H F Bond n-C₅H₁₁ 353 HH H F Bond n-C₆H₁₃ 354 H H H F Bond n-C₇H₁₅ 355 H H F F Bond CH₃ 356 H HF F Bond C₂H₅ 357 H H F F Bond n-C₃H₇ 358 H H F F Bond n-C₄H₉ 359 H H FF Bond n-C₅H₁₁ 360 H H F F Bond n-C₆H₁₃ 361 H H F F Bond n-C₇H₁₅ 362 H FF F Bond CH₃ 363 H F F F Bond C₂H₅ 364 H F F F Bond n-C₃H₇ 365 H F F FBond n-C₄H₉ 366 H F F F Bond n-C₅H₁₁ 367 H F F F Bond n-C₆H₁₃ 368 H F FF Bond n-C₇H₁₅ 369 H F F F CF₂CF₂ CH₃ 370 H F F F CF₂CF₂ C₂H₅ 371 H F FF CF₂CF₂ n-C₃H₇ 372 H F F F CF₂CF₂ n-C₄H₉ 373 H F F F CF₂CF₂ n-C₅H₁₁ 374H F F F CF₂CF₂ n-C₆H₁₃ 375 H F F F CF₂CF₂ n-C₇H₁₅ 376 H F F F CF₂O CH₃377 H F F F CF₂O C₂H₅ 378 H F F F CF₂O n-C₃H₇ 379 H F F F CF₂O n-C₄H₉380 H F F F CF₂O n-C₅H₁₁ 381 H F F F CF₂O n-C₆H₁₃ 382 H F F F CF₂On-C₇H₁₅ 383 CH₃ H F F Bond CH₃ 384 CH₃ H F F Bond C₂H₅ 385 CH₃ H F FBond n-C₃H₇ 386 CH₃ H F F Bond n-C₄H₉ 387 CH₃ H F F Bond n-C₅H₁₁ 388 CH₃H F F Bond n-C₆H₁₃ 389 CH₃ H F F Bond n-C₇H₁₅ 390 CH₃ F F F Bond CH₃ 391CH₃ F F F Bond C₂H₅ 392 CH₃ F F F Bond n-C₃H₇ 393 CH₃ F F F Bond n-C₄H₉394 CH₃ F F F Bond n-C₅H₁₁ 395 CH₃ F F F Bond n-C₆H₁₃ 396 CH₃ F F F Bondn-C₇H₁₅ 397 CH₃ F F F CF₂CF₂ CH₃ 398 CH₃ F F F CF₂CF₂ C₂H₅ 399 CH₃ F F FCF₂CF₂ n-C₃H₇ 400 CH₃ F F F CF₂CF₂ n-C₄H₉ 401 CH₃ F F F CF₂CF₂ n-C₅H₁₁402 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 403 CH₃ F F F CF₂CF₂ n-C₇H₁₅ 404 CH₃ F F FCF₂O CH₃ 405 CH₃ F F F CF₂O C₂H₅ 406 CH₃ F F F CF₂O n-C₃H₇ 407 CH₃ F F FCF₂O n-C₄H₉ 408 CH₃ F F F CF₂O n-C₅H₁₁ 409 CH₃ F F F CF₂O n-C₆H₁₃ 410CH₃ F F F CF₂O n-C₇H₁₅ 411 C₂H₅ H F F Bond CH₃ 412 C₂H₅ H F F Bond C₂H₅413 C₂H₅ H F F Bond n-C₃H₇ 414 C₂H₅ H F F Bond n-C₄H₉ 415 C₂H₅ H F FBond n-C₅H₁₁ 416 C₂H₅ H F F Bond n-C₆H₁₃ 417 C₂H₅ H F F Bond n-C₇H₁₅ 418C₂H₅ F F F Bond CH₃ 419 C₂H₅ F F F Bond C₂H₅ 420 C₂H₅ F F F Bond n-C₃H₇421 C₂H₅ F F F Bond n-C₄H₉ 422 C₂H₅ F F F Bond n-C₅H₁₁ 423 C₂H₅ F F FBond n-C₆H₁₃ 424 C₂H₅ F F F Bond n-C₇H₁₅ 425 n-C₃H₇ H F F Bond CH₃ 426n-C₃H₇ H F F Bond C₂H₅ 427 n-C₃H₇ H F F Bond n-C₃H₇ 428 n-C₃H₇ H F FBond n-C₄H₉ 429 n-C₃H₇ H F F Bond n-C₅H₁₁ 430 n-C₃H₇ H F F Bond n-C₆H₁₃431 n-C₃H₇ H F F Bond n-C₇H₁₅ 432 n-C₃H₇ F F F Bond CH₃ 433 n-C₃H₇ F F FBond C₂H₅ 434 n-C₃H₇ F F F Bond n-C₃H₇ 435 n-C₃H₇ F F F Bond n-C₄H₉ 436n-C₃H₇ F F F Bond n-C₅H₁₁ 437 n-C₃H₇ F F F Bond n-C₆H₁₃ 438 n-C₃H₇ F F FBond n-C₇H₁₅ 439 n-C₄H₉ H F F Bond CH₃ 440 n-C₄H₉ H F F Bond C₂H₅ 441n-C₄H₉ H F F Bond n-C₃H₇ 442 n-C₄H₉ H F F Bond n-C₄H₉ 443 n-C₄H₉ H F FBond n-C₅H₁₁ 444 n-C₄H₉ H F F Bond n-C₆H₁₃ 445 n-C₄H₉ H F F Bond n-C₇H₁₅446 n-C₄H₉ F F F Bond CH₃ 447 n-C₄H₉ F F F Bond C₂H₅ 448 n-C₄H₉ F F FBond n-C₃H₇ 449 n-C₄H₉ F F F Bond n-C₄H₉ 450 n-C₄H₉ F F F Bond n-C₅H₁₁451 n-C₄H₉ F F F Bond n-C₆H₁₃ 452 n-C₄H₉ F F F Bond n-C₇H₁₅ 453 n-C₅H₁₁H F F Bond CH₃ 454 n-C₅H₁₁ H F F Bond C₂H₅ 455 n-C₅H₁₁ H F F Bond n-C₃H₇456 n-C₅H₁₁ H F F Bond n-C₄H₉ 457 n-C₅H₁₁ H F F Bond n-C₅H₁₁ 458 n-C₅H₁₁H F F Bond n-C₆H₁₃ 459 n-C₅H₁₁ H F F Bond n-C₇H₁₅ 460 n-C₅H₁₁ F F F BondCH₃ 461 n-C₅H₁₁ F F F Bond C₂H₅ 462 n-C₅H₁₁ F F F Bond n-C₃H₇ 463n-C₅H₁₁ F F F Bond n-C₄H₉ 464 n-C₅H₁₁ F F F Bond n-C₅H₁₁ 465 n-C₅H₁₁ F FF Bond n-C₆H₁₃ 466 n-C₅H₁₁ F F F Bond n-C₇H₁₅

Examples 467-549

Example R^(b) X¹ X² X³ Z R^(a) 467 CH₃ H F F Bond CH₃ 468 CH₃ H F F BondC₂H₅ 469 CH₃ H F F Bond n-C₃H₇ 470 CH₃ H F F Bond n-C₄H₉ 471 CH₃ H F FBond n-C₅H₁₁ 472 CH₃ H F F Bond n-C₆H₁₃ 473 CH₃ H F F Bond n-C₇H₁₅ 474CH₃ F F F Bond CH₃ 475 CH₃ F F F Bond C₂H₅ 476 CH₃ F F F Bond n-C₃H₇ 477CH₃ F F F Bond n-C₄H₉ 478 CH₃ F F F Bond n-C₅H₁₁ 479 CH₃ F F F Bondn-C₆H₁₃ 480 CH₃ F F F Bond n-C₇H₁₅ 481 CH₃ F F F CF₂CF₂ CH₃ 482 CH₃ F FF CF₂CF₂ C₂H₅ 483 CH₃ F F F CF₂CF₂ n-C₃H₇ 484 CH₃ F F F CF₂CF₂ n-C₄H₉485 CH₃ F F F CF₂CF₂ n-C₅H₁₁ 486 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 487 CH₃ F F FCF₂CF₂ n-C₇H₁₅ 488 C₂H₅ H F F Bond CH₃ 489 C₂H₅ H F F Bond C₂H₅ 490 C₂H₅H F F Bond n-C₃H₇ 491 C₂H₅ H F F Bond n-C₄H₉ 492 C₂H₅ H F F Bond n-C₅H₁₁493 C₂H₅ H F F Bond n-C₆H₁₃ 494 C₂H₅ H F F Bond n-C₇H₁₅ 495 C₂H₅ F F FCF₂CF₂ CH₃ 496 C₂H₅ F F F CF₂CF₂ C₂H₅ 497 C₂H₅ F F F CF₂CF₂ n-C₃H₇ 498C₂H₅ F F F CF₂CF₂ n-C₄H₉ 499 C₂H₅ F F F CF₂CF₂ n-C₅H₁₁ 500 C₂H₅ F F FCF₂CF₂ n-C₆H₁₃ 501 C₂H₅ F F F CF₂CF₂ n-C₇H₁₅ 502 C₂H₅ F F F Bond CH₃ 503C₂H₅ F F F Bond C₂H₅ 504 C₂H₅ F F F Bond n-C₃H₇ 505 C₂H₅ F F F Bondn-C₄H₉ 506 C₂H₅ F F F Bond n-C₅H₁₁ 507 C₂H₅ F F F Bond n-C₆H₁₃ 508 C₂H₅F F F Bond n-C₇H₁₅ 509 n-C₃H₇ H F F Bond CH₃ 510 n-C₃H₇ H F F Bond C₂H₅511 n-C₃H₇ H F F Bond n-C₃H₇ 512 n-C₃H₇ H F F Bond n-C₄H₉ 513 n-C₃H₇ H FF Bond n-C₅H₁₁ 514 n-C₃H₇ H F F Bond n-C₆H₁₃ 515 n-C₃H₇ H F F Bondn-C₇H₁₅ 516 n-C₃H₇ F F F Bond CH₃ 517 n-C₃H₇ F F F Bond C₂H₅ 518 n-C₃H₇F F F Bond n-C₄H₉ 519 n-C₃H₇ F F F Bond n-C₅H₁₁ 520 n-C₃H₇ F F F Bondn-C₆H₁₃ 521 n-C₃H₇ F F F Bond n-C₇H₁₅ 522 n-C₄H₉ H F F Bond CH₃ 523n-C₄H₉ H F F Bond C₂H₅ 524 n-C₄H₉ H F F Bond n-C₃H₇ 525 n-C₄H₉ H F FBond n-C₄H₉ 526 n-C₄H₉ H F F Bond n-C₅H₁₁ 527 n-C₄H₉ H F F Bond n-C₆H₁₃528 n-C₄H₉ H F F Bond n-C₇H₁₅ 529 n-C₄H₉ F F F Bond CH₃ 530 n-C₄H₉ F F FBond C₂H₅ 531 n-C₄H₉ F F F Bond n-C₃H₇ 532 n-C₄H₉ F F F Bond n-C₄H₉ 533n-C₄H₉ F F F Bond n-C₅H₁₁ 534 n-C₄H₉ F F F Bond n-C₆H₁₃ 535 n-C₄H₉ F F FBond n-C₇H₁₅ 536 n-C₅H₁₁ H F F Bond CH₃ 537 n-C₅H₁₁ H F F Bond C₂H₅ 538n-C₅H₁₁ H F F Bond n-C₃H₇ 539 n-C₅H₁₁ H F F Bond n-C₄H₉ 540 n-C₅H₁₁ H FF Bond n-C₅H₁₁ 541 n-C₅H₁₁ H F F Bond n-C₆H₁₃ 542 n-C₅H₁₁ H F F Bondn-C₇H₁₅ 543 n-C₅H₁₁ F F F Bond CH₃ 544 n-C₅H₁₁ F F F Bond C₂H₅ 545n-C₅H₁₁ F F F Bond n-C₃H₇ 546 n-C₅H₁₁ F F F Bond n-C₄H₉ 547 n-C₅H₁₁ F FF Bond n-C₅H₁₁ 548 n-C₅H₁₁ F F F Bond n-C₆H₁₃ 549 n-C₅H₁₁ F F F Bondn-C₇H₁₅

Examples 550-646

Example R^(b) X¹ X² X³ Z R^(a) 550 CH₃ H F F Bond CH₃ 551 CH₃ H F F BondC₂H₅ 552 CH₃ H F F Bond n-C₃H₇ 553 CH₃ H F F Bond n-C₄H₉ 554 CH₃ H F FBond n-C₅H₁₁ 555 CH₃ H F F Bond n-C₆H₁₃ 556 CH₃ H F F Bond n-C₇H₁₅ 557CH₃ F F F Bond CH₃ 558 CH₃ F F F Bond C₂H₅ 559 CH₃ F F F Bond n-C₃H₇ 560CH₃ F F F Bond n-C₄H₉ 561 CH₃ F F F Bond n-C₅H₁₁ 562 CH₃ F F F Bondn-C₆H₁₃ 563 CH₃ F F F Bond n-C₇H₁₅ 564 CH₃ F F F CF₂CF₂ CH₃ 565 CH₃ F FF CF₂CF₂ C₂H₅ 566 CH₃ F F F CF₂CF₂ n-C₃H₇ 567 CH₃ F F F CF₂CF₂ n-C₄H₉568 CH₃ F F F CF₂CF₂ n-C₅H₁₁ 569 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 570 CH₃ F F FCF₂CF₂ n-C₇H₁₅ 571 CH₃ F F F CF₂O CH₃ 572 CH₃ F F F CF₂O C₂H₅ 573 CH₃ FF F CF₂O n-C₃H₇ 574 CH₃ F F F CF₂O n-C₄H₉ 575 CH₃ F F F CF₂O n-C₅H₁₁ 576CH₃ F F F CF₂O n-C₆H₁₃ 577 CH₃ F F F CF₂O n-C₇H₁₅ 578 C₂H₅ H F F BondCH₃ 579 C₂H₅ H F F Bond C₂H₅ 580 C₂H₅ H F F Bond n-C₃H₇ 581 C₂H₅ H F FBond n-C₄H₉ 582 C₂H₅ H F F Bond n-C₅H₁₁ 583 C₂H₅ H F F Bond n-C₆H₁₃ 584C₂H₅ H F F Bond n-C₇H₁₅ 585 C₂H₅ F F F CF₂CF₂ CH₃ 586 C₂H₅ F F F CF₂CF₂C₂H₅ 587 C₂H₅ F F F CF₂CF₂ n-C₄H₉ 588 C₂H₅ F F F CF₂CF₂ n-C₅H₁₁ 589 C₂H₅F F F CF₂CF₂ n-C₆H₁₃ 590 C₂H₅ F F F CF₂CF₂ n-C₇H₁₅ 591 C₂H₅ F F F CF₂OCH₃ 592 C₂H₅ F F F CF₂O C₂H₅ 593 C₂H₅ F F F CF₂O n-C₃H₇ 594 C₂H₅ F F FCF₂O n-C₄H₉ 595 C₂H₅ F F F CF₂O n-C₅H₁₁ 596 C₂H₅ F F F CF₂O n-C₆H₁₃ 597C₂H₅ F F F CF₂O n-C₇H₁₅ 598 C₂H₅ F F F Bond CH₃ 599 C₂H₅ F F F Bond C₂H₅600 C₂H₅ F F F Bond n-C₃H₇ 601 C₂H₅ F F F Bond n-C₄H₉ 602 C₂H₅ F F FBond n-C₅H₁₁ 603 C₂H₅ F F F Bond n-C₆H₁₃ 604 C₂H₅ F F F Bond n-C₇H₁₅ 605n-C₃H₇ H F F Bond CH₃ 606 n-C₃H₇ H F F Bond C₂H₅ 607 n-C₃H₇ H F F Bondn-C₃H₇ 608 n-C₃H₇ H F F Bond n-C₄H₉ 609 n-C₃H₇ H F F Bond n-C₅H₁₁ 610n-C₃H₇ H F F Bond n-C₆H₁₃ 611 n-C₃H₇ H F F Bond n-C₇H₁₅ 612 n-C₃H₇ F F FBond CH₃ 613 n-C₃H₇ F F F Bond C₂H₅ 614 n-C₃H₇ F F F Bond n-C₃H₇ 615n-C₃H₇ F F F Bond n-C₄H₉ 616 n-C₃H₇ F F F Bond n-C₅H₁₁ 617 n-C₃H₇ F F FBond n-C₆H₁₃ 618 n-C₃H₇ F F F Bond n-C₇H₁₅ 619 n-C₄H₉ H F F Bond CH₃ 620n-C₄H₉ H F F Bond C₂H₅ 621 n-C₄H₉ H F F Bond n-C₃H₇ 622 n-C₄H₉ H F FBond n-C₄H₉ 623 n-C₄H₉ H F F Bond n-C₅H₁₁ 624 n-C₄H₉ H F F Bond n-C₆H₁₃625 n-C₄H₉ H F F Bond n-C₇H₁₅ 626 n-C₄H₉ F F F Bond CH₃ 627 n-C₄H₉ F F FBond C₂H₅ 628 n-C₄H₉ F F F Bond n-C₃H₇ 629 n-C₄H₉ F F F Bond n-C₄H₉ 630n-C₄H₉ F F F Bond n-C₅H₁₁ 631 n-C₄H₉ F F F Bond n-C₆H₁₃ 632 n-C₄H₉ F F FBond n-C₇H₁₅ 633 n-C₅H₁₁ H F F Bond CH₃ 634 n-C₅H₁₁ H F F Bond C₂H₅ 635n-C₅H₁₁ H F F Bond n-C₃H₇ 636 n-C₅H₁₁ H F F Bond n-C₄H₉ 637 n-C₅H₁₁ H FF Bond n-C₅H₁₁ 638 n-C₅H₁₁ H F F Bond n-C₆H₁₃ 639 n-C₅H₁₁ H F F Bondn-C₇H₁₅ 640 n-C₅H₁₁ F F F Bond CH₃ 641 n-C₅H₁₁ F F F Bond C₂H₅ 642n-C₅H₁₁ F F F Bond n-C₃H₇ 643 n-C₅H₁₁ F F F Bond n-C₄H₉ 644 n-C₅H₁₁ F FF Bond n-C₅H₁₁ 645 n-C₅H₁₁ F F F Bond n-C₆H₁₃ 646 n-C₅H₁₁ F F F Bondn-C₇H₁₅

Examples 647-765

Example E¹ X^(1a) X^(1b) X² X³ R 647 H H H H H CH₃ 648 H H H H H C₂H₅649 H H H H H n-C₃H₇ 650 H H H H H n-C₄H₉ 651 H H H H H n-C₅H₁₁ 652 H HH H H n-C₆H₁₃ 653 H H H H H n-C₇H₁₅ 654 H H H H F CH₃ 655 H H H H F C₂H₅656 H H H H F n-C₃H₇ 657 H H H H F n-C₄H₉ 658 H H H H F n-C₅H₁₁ 659 H HH H F n-C₆H₁₃ 660 H H H H F n-C₇H₁₅ 661 H H H F F CH₃ 662 H H H F F C₂H₅663 H H H F F n-C₃H₇ 664 H H H F F n-C₄H₉ 665 H H H F F n-C₅H₁₁ 666 H HH F F n-C₆H₁₃ 667 H H H F F n-C₇H₁₅ 668 H H F F F CH₃ 669 H H F F F C₂H₅670 H H F F F n-C₃H₇ 671 H H F F F n-C₄H₉ 672 H H F F F n-C₅H₁₁ 673 H HF F F n-C₆H₁₃ 674 H H F F F n-C₇H₁₅ 675 H F F F F CH₃ 676 H F F F F C₂H₅677 H F F F F n-C₃H₇ 678 H F F F F n-C₄H₉ 679 H F F F F n-C₅H₁₁ 680 H FF F F n-C₆H₁₃ 681 H F F F F n-C₇H₁₅ 682 CH₃ H H F F CH₃ 683 CH₃ H H F FC₂H₅ 684 CH₃ H H F F n-C₃H₇ 685 CH₃ H H F F n-C₄H₉ 686 CH₃ H H F Fn-C₅H₁₁ 687 CH₃ H H F F n-C₆H₁₃ 688 CH₃ H H F F n-C₇H₁₅ 689 CH₃ H F F FCH₃ 690 CH₃ H F F F C₂H₅ 691 CH₃ H F F F n-C₃H₇ 692 CH₃ H F F F n-C₄H₉693 CH₃ H F F F n-C₅H₁₁ 694 CH₃ H F F F n-C₆H₁₃ 695 CH₃ H F F F n-C₇H₁₅696 CH₃ F F F F CH₃ 697 CH₃ F F F F C₂H₅ 698 CH₃ F F F F n-C₃H₇ 699 CH₃F F F F n-C₄H₉ 700 CH₃ F F F F n-C₅H₁₁ 701 CH₃ F F F F n-C₆H₁₃ 702 CH₃ FF F F n-C₇H₁₅ 703 C₂H₅ H H F F CH₃ 704 C₂H₅ H H F F C₂H₅ 705 C₂H₅ H H FF n-C₃H₇ 706 C₂H₅ H H F F n-C₄H₉ 707 C₂H₅ H H F F n-C₅H₁₁ 708 C₂H₅ H H FF n-C₆H₁₃ 709 C₂H₅ H H F F n-C₇H₁₅ 710 C₂H₅ H F F F CH₃ 711 C₂H₅ H F F FC₂H₅ 712 C₂H₅ H F F F n-C₃H₇ 713 C₂H₅ H F F F n-C₄H₉ 714 C₂H₅ H F F Fn-C₅H₁₁ 715 C₂H₅ H F F F n-C₆H₁₃ 716 C₂H₅ H F F F n-C₇H₁₅ 717 C₂H₅ F F FF CH₃ 718 C₂H₅ F F F F C₂H₅ 719 C₂H₅ F F F F n-C₃H₇ 720 C₂H₅ F F F Fn-C₄H₉ 721 C₂H₅ F F F F n-C₅H₁₁ 722 C₂H₅ F F F F n-C₆H₁₃ 723 C₂H₅ F F FF n-C₇H₁₅ 724 n-C₃H₇ H H F F CH₃ 725 n-C₃H₇ H H F F C₂H₅ 726 n-C₃H₇ H HF F n-C₃H₇ 727 n-C₃H₇ H H F F n-C₄H₉ 728 n-C₃H₇ H H F F n-C₅H₁₁ 729n-C₃H₇ H H F F n-C₆H₁₃ 730 n-C₃H₇ H H F F n-C₇H₁₅ 731 n-C₃H₇ F F F F CH₃732 n-C₃H₇ F F F F C₂H₅ 733 n-C₃H₇ F F F F n-C₃H₇ 734 n-C₃H₇ F F F Fn-C₄H₉ 735 n-C₃H₇ F F F F n-C₅H₁₁ 736 n-C₃H₇ F F F F n-C₆H₁₃ 737 n-C₃H₇F F F F n-C₇H₁₅ 738 n-C₄H₉ H H F F CH₃ 739 n-C₄H₉ H H F F C₂H₅ 740n-C₄H₉ H H F F n-C₃H₇ 741 n-C₄H₉ H H F F n-C₄H₉ 742 n-C₄H₉ H H F Fn-C₅H₁₁ 743 n-C₄H₉ H H F F n-C₆H₁₃ 744 n-C₄H₉ H H F F n-C₇H₁₅ 745 n-C₄H₉F F F F CH₃ 746 n-C₄H₉ F F F F C₂H₅ 747 n-C₄H₉ F F F F n-C₃H₇ 748 n-C₄H₉F F F F n-C₄H₉ 749 n-C₄H₉ F F F F n-C₅H₁₁ 750 n-C₄H₉ F F F F n-C₆H₁₃ 751n-C₄H₉ F F F F n-C₇H₁₅ 752 n-C₅H₁₁ H H F F CH₃ 753 n-C₅H₁₁ H H F F C₂H₅754 n-C₅H₁₁ H H F F n-C₃H₇ 755 n-C₅H₁₁ H H F F n-C₄H₉ 756 n-C₅H₁₁ H H FF n-C₅H₁₁ 757 n-C₅H₁₁ H H F F n-C₆H₁₃ 758 n-C₅H₁₁ H H F F n-C₇H₁₅ 759n-C₅H₁₁ F F F F CH₃ 760 n-C₅H₁₁ F F F F C₂H₅ 761 n-C₅H₁₁ F F F F n-C₃H₇762 n-C₅H₁₁ F F F F n-C₄H₉ 763 n-C₅H₁₁ F F F F n-C₅H₁₁ 764 n-C₅H₁₁ F F FF n-C₆H₁₃ 765 n-C₅H₁₁ F F F F n-C₇H₁₅

Examples 766-912

Example E¹ X^(1a) X^(1b) X² X³ Z R 766 H H H H F Bond CH₃ 767 H H H H FBond C₂H₅ 768 H H H H F Bond n-C₃H₇ 769 H H H H F Bond n-C₄H₉ 770 H H HH F Bond n-C₅H₁₁ 771 H H H H F Bond n-C₆H₁₃ 772 H H H H F Bond n-C₇H₁₅773 H H H F F Bond CH₃ 774 H H H F F Bond C₂H₅ 775 H H H F F Bond n-C₃H₇776 H H H F F Bond n-C₄H₉ 777 H H H F F Bond n-C₅H₁₁ 778 H H H F F Bondn-C₆H₁₃ 779 H H H F F Bond n-C₇H₁₅ 780 H H F F F Bond CH₃ 781 H H F F FBond C₂H₅ 782 H H F F F Bond n-C₃H₇ 783 H H F F F Bond n-C₄H₉ 784 H H FF F Bond n-C₅H₁₁ 785 H H F F F Bond n-C₆H₁₃ 786 H H F F F Bond n-C₇H₁₅787 H F F F F Bond CH₃ 788 H F F F F Bond C₂H₅ 789 H F F F F Bond n-C₃H₇790 H F F F F Bond n-C₄H₉ 791 H F F F F Bond n-C₅H₁₁ 792 H F F F F Bondn-C₆H₁₃ 793 H F F F F Bond n-C₇H₁₅ 794 H H F F F CF₂CF₂ CH₃ 795 H H F FF CF₂CF₂ C₂H₅ 796 H H F F F CF₂CF₂ n-C₃H₇ 797 H H F F F CF₂CF₂ n-C₄H₉798 H H F F F CF₂CF₂ n-C₅H₁₁ 799 H H F F F CF₂CF₂ n-C₆H₁₃ 800 H H F F FCF₂CF₂ n-C₇H₁₅ 801 H F F F F CF₂CF₂ CH₃ 802 H F F F F CF₂CF₂ C₂H₅ 803 HF F F F CF₂CF₂ n-C₃H₇ 804 H F F F F CF₂CF₂ n-C₄H₉ 805 H F F F F CF₂CF₂n-C₅H₁₁ 806 H F F F F CF₂CF₂ n-C₆H₁₃ 807 H F F F F CF₂CF₂ n-C₇H₁₅ 808 HF F F F OCF₂ CH₃ 809 H F F F F OCF₂ C₂H₅ 810 H F F F F OCF₂ n-C₃H₇ 811 HF F F F OCF₂ n-C₄H₉ 812 H F F F F OCF₂ n-C₅H₁₁ 813 H F F F F OCF₂n-C₆H₁₃ 814 H F F F F OCF₂ n-C₇H₁₅ 815 CH₃ H H F F Bond CH₃ 816 CH₃ H HF F Bond C₂H₅ 817 CH₃ H H F F Bond n-C₃H₇ 818 CH₃ H H F F Bond n-C₄H₉819 CH₃ H H F F Bond n-C₅H₁₁ 820 CH₃ H H F F Bond n-C₆H₁₃ 821 CH₃ H H FF Bond n-C₇H₁₅ 822 CH₃ H F F F Bond CH₃ 823 CH₃ H F F F Bond C₂H₅ 824CH₃ H F F F Bond n-C₃H₇ 825 CH₃ H F F F Bond n-C₄H₉ 826 CH₃ H F F F Bondn-C₅H₁₁ 827 CH₃ H F F F Bond n-C₆H₁₃ 828 CH₃ H F F F Bond n-C₇H₁₅ 829CH₃ F F F F Bond CH₃ 830 CH₃ F F F F Bond C₂H₅ 831 CH₃ F F F F Bondn-C₃H₇ 832 CH₃ F F F F Bond n-C₄H₉ 833 CH₃ F F F F Bond n-C₅H₁₁ 834 CH₃F F F F Bond n-C₆H₁₃ 835 CH₃ F F F F Bond n-C₇H₁₅ 836 CH₃ F F F F CF₂CF₂CH₃ 837 CH₃ F F F F CF₂CF₂ C₂H₅ 838 CH₃ F F F F CF₂CF₂ n-C₃H₇ 839 CH₃ FF F F CF₂CF₂ n-C₄H₉ 840 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 841 CH₃ F F F FCF₂CF₂ n-C₆H₁₃ 842 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 843 CH₃ F F F F OCF₂ CH₃844 CH₃ F F F F OCF₂ C₂H₅ 845 CH₃ F F F F OCF₂ n-C₃H₇ 846 CH₃ F F F FOCF₂ n-C₄H₉ 847 CH₃ F F F F OCF₂ n-C₅H₁₁ 848 CH₃ F F F F OCF₂ n-C₆H₁₃849 CH₃ F F F F OCF₂ n-C₇H₁₅ 850 C₂H₅ H H F F Bond CH₃ 851 C₂H₅ H H F FBond C₂H₅ 852 C₂H₅ H H F F Bond n-C₃H₇ 853 C₂H₅ H H F F Bond n-C₄H₉ 854C₂H₅ H H F F Bond n-C₅H₁₁ 855 C₂H₅ H H F F Bond n-C₆H₁₃ 856 C₂H₅ H H F FBond n-C₇H₁₅ 857 C₂H₅ F F F F Bond CH₃ 858 C₂H₅ F F F F Bond C₂H₅ 859C₂H₅ F F F F Bond n-C₃H₇ 860 C₂H₅ F F F F Bond n-C₄H₉ 861 C₂H₅ F F F FBond n-C₅H₁₁ 862 C₂H₅ F F F F Bond n-C₆H₁₃ 863 C₂H₅ F F F F Bond n-C₇H₁₅864 n-C₃H₇ H H F F Bond CH₃ 865 n-C₃H₇ H H F F Bond C₂H₅ 866 n-C₃H₇ H HF F Bond n-C₃H₇ 867 n-C₃H₇ H H F F Bond n-C₄H₉ 868 n-C₃H₇ H H F F Bondn-C₅H₁₁ 869 n-C₃H₇ H H F F Bond n-C₆H₁₃ 870 n-C₃H₇ H H F F Bond n-C₇H₁₅871 n-C₃H₇ H F F F Bond CH₃ 872 n-C₃H₇ H F F F Bond C₂H₅ 873 n-C₃H₇ H FF F Bond n-C₃H₇ 874 n-C₃H₇ H F F F Bond n-C₄H₉ 875 n-C₃H₇ H F F F Bondn-C₅H₁₁ 876 n-C₃H₇ H F F F Bond n-C₆H₁₃ 877 n-C₃H₇ H F F F Bond n-C₇H₁₅878 n-C₃H₇ F F F F Bond CH₃ 879 n-C₃H₇ F F F F Bond C₂H₅ 880 n-C₃H₇ F FF F Bond n-C₃H₇ 881 n-C₃H₇ F F F F Bond n-C₄H₉ 882 n-C₃H₇ F F F F Bondn-C₅H₁₁ 883 n-C₃H₇ F F F F Bond n-C₆H₁₃ 884 n-C₃H₇ F F F F Bond n-C₇H₁₅885 n-C₄H₉ H H F F Bond CH₃ 886 n-C₄H₉ H H F F Bond C₂H₅ 887 n-C₄H₉ H HF F Bond n-C₃H₇ 888 n-C₄H₉ H H F F Bond n-C₄H₉ 889 n-C₄H₉ H H F F Bondn-C₅H₁₁ 890 n-C₄H₉ H H F F Bond n-C₆H₁₃ 891 n-C₄H₉ H H F F Bond n-C₇H₁₅892 n-C₄H₉ F F F F Bond CH₃ 893 n-C₄H₉ F F F F Bond C₂H₅ 894 n-C₄H₉ F FF F Bond n-C₃H₇ 895 n-C₄H₉ F F F F Bond n-C₄H₉ 896 n-C₄H₉ F F F F Bondn-C₅H₁₁ 897 n-C₄H₉ F F F F Bond n-C₆H₁₃ 898 n-C₄H₉ F F F F Bond n-C₇H₁₅899 n-C₅H₁₁ H H F F Bond CH₃ 900 n-C₅H₁₁ H H F F Bond C₂H₅ 901 n-C₅H₁₁ HH F F Bond n-C₃H₇ 902 n-C₅H₁₁ H H F F Bond n-C₄H₉ 903 n-C₅H₁₁ H H F FBond n-C₅H₁₁ 904 n-C₅H₁₁ H H F F Bond n-C₆H₁₃ 905 n-C₅H₁₁ H H F F Bondn-C₇H₁₅ 906 n-C₅H₁₁ F F F F Bond CH₃ 907 n-C₅H₁₁ F F F F Bond C₂H₅ 908n-C₅H₁₁ F F F F Bond n-C₃H₇ 909 n-C₅H₁₁ F F F F Bond n-C₄H₉ 910 n-C₅H₁₁F F F F Bond n-C₅H₁₁ 911 n-C₅H₁₁ F F F F Bond n-C₆H₁₃ 912 n-C₅H₁₁ F F FF Bond n-C₇H₁₅

Examples 913-1059

Example E¹ X^(1a) X^(1b) X² X³ Z R 913 H H H H F Bond CH₃ 914 H H H H FBond C₂H₅ 915 H H H H F Bond n-C₃H₇ 916 H H H H F Bond n-C₄H₉ 917 H H HH F Bond n-C₅H₁₁ 918 H H H H F Bond n-C₆H₁₃ 919 H H H H F Bond n-C₇H₁₅920 H H H F F Bond CH₃ 921 H H H F F Bond C₂H₅ 922 H H H F F Bond n-C₃H₇923 H H H F F Bond n-C₄H₉ 924 H H H F F Bond n-C₅H₁₁ 925 H H H F F Bondn-C₆H₁₃ 926 H H H F F Bond n-C₇H₁₅ 927 H H F F F Bond CH₃ 928 H H F F FBond C₂H₅ 929 H H F F F Bond n-C₃H₇ 930 H H F F F Bond n-C₄H₉ 931 H H FF F Bond n-C₅H₁₁ 932 H H F F F Bond n-C₆H₁₃ 933 H H F F F Bond n-C₇H₁₅934 H F F F F Bond CH₃ 935 H F F F F Bond C₂H₅ 936 H F F F F Bond n-C₃H₇937 H F F F F Bond n-C₄H₉ 938 H F F F F Bond n-C₅H₁₁ 939 H F F F F Bondn-C₆H₁₃ 940 H F F F F Bond n-C₇H₁₅ 941 H H F F F CF₂CF₂ CH₃ 942 H H F FF CF₂CF₂ C₂H₅ 943 H H F F F CF₂CF₂ n-C₃H₇ 944 H H F F F CF₂CF₂ n-C₄H₉945 H H F F F CF₂CF₂ n-C₅H₁₁ 946 H H F F F CF₂CF₂ n-C₆H₁₃ 947 H H F F FCF₂CF₂ n-C₇H₁₅ 948 H F F F F CF₂CF₂ CH₃ 949 H F F F F CF₂CF₂ C₂H₅ 950 HF F F F CF₂CF₂ n-C₃H₇ 951 H F F F F CF₂CF₂ n-C₄H₉ 952 H F F F F CF₂CF₂n-C₅H₁₁ 953 H F F F F CF₂CF₂ n-C₆H₁₃ 954 H F F F F CF₂CF₂ n-C₇H₁₅ 955 HF F F F CF₂O CH₃ 956 H F F F F CF₂O C₂H₅ 957 H F F F F CF₂O n-C₃H₇ 958 HF F F F CF₂O n-C₄H₉ 959 H F F F F CF₂O n-C₅H₁₁ 960 H F F F F CF₂On-C₆H₁₃ 961 H F F F F CF₂O n-C₇H₁₅ 962 CH₃ H H F F Bond CH₃ 963 CH₃ H HF F Bond C₂H₅ 964 CH₃ H H F F Bond n-C₃H₇ 965 CH₃ H H F F Bond n-C₄H₉966 CH₃ H H F F Bond n-C₅H₁₁ 967 CH₃ H H F F Bond n-C₆H₁₃ 968 CH₃ H H FF Bond n-C₇H₁₅ 969 CH₃ H F F F Bond CH₃ 970 CH₃ H F F F Bond C₂H₅ 971CH₃ H F F F Bond n-C₃H₇ 972 CH₃ H F F F Bond n-C₄H₉ 973 CH₃ H F F F Bondn-C₅H₁₁ 974 CH₃ H F F F Bond n-C₆H₁₃ 975 CH₃ H F F F Bond n-C₇H₁₅ 976CH₃ F F F F Bond CH₃ 977 CH₃ F F F F Bond C₂H₅ 978 CH₃ F F F F Bondn-C₃H₇ 979 CH₃ F F F F Bond n-C₄H₉ 980 CH₃ F F F F Bond n-C₅H₁₁ 981 CH₃F F F F Bond n-C₆H₁₃ 982 CH₃ F F F F Bond n-C₇H₁₅ 983 CH₃ F F F F CF₂CF₂CH₃ 984 CH₃ F F F F CF₂CF₂ C₂H₅ 985 CH₃ F F F F CF₂CF₂ n-C₃H₇ 986 CH₃ FF F F CF₂CF₂ n-C₄H₉ 987 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 988 CH₃ F F F FCF₂CF₂ n-C₆H₁₃ 989 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 990 CH₃ F F F F CF₂O CH₃991 CH₃ F F F F CF₂O C₂H₅ 992 CH₃ F F F F CF₂O n-C₃H₇ 993 CH₃ F F F FCF₂O n-C₄H₉ 994 CH₃ F F F F CF₂O n-C₅H₁₁ 995 CH₃ F F F F CF₂O n-C₆H₁₃996 CH₃ F F F F CF₂O n-C₇H₁₅ 997 C₂H₅ H H F F Bond CH₃ 998 C₂H₅ H H F FBond C₂H₅ 999 C₂H₅ H H F F Bond n-C₃H₇ 1000 C₂H₅ H H F F Bond n-C₄H₉1001 C₂H₅ H H F F Bond n-C₅H₁₁ 1002 C₂H₅ H H F F Bond n-C₆H₁₃ 1003 C₂H₅H H F F Bond n-C₇H₁₅ 1004 C₂H₅ F F F F Bond CH₃ 1005 C₂H₅ F F F F BondC₂H₅ 1006 C₂H₅ F F F F Bond n-C₃H₇ 1007 C₂H₅ F F F F Bond n-C₄H₉ 1008C₂H₅ F F F F Bond n-C₅H₁₁ 1009 C₂H₅ F F F F Bond n-C₆H₁₃ 1010 C₂H₅ F F FF Bond n-C₇H₁₅ 1011 n-C₃H₇ H H F F Bond CH₃ 1012 n-C₃H₇ H H F F BondC₂H₅ 1013 n-C₃H₇ H H F F Bond n-C₃H₇ 1014 n-C₃H₇ H H F F Bond n-C₄H₉1015 n-C₃H₇ H H F F Bond n-C₅H₁₁ 1016 n-C₃H₇ H H F F Bond n-C₆H₁₃ 1017n-C₃H₇ H H F F Bond n-C₇H₁₅ 1018 n-C₃H₇ H F F F Bond CH₃ 1019 n-C₃H₇ H FF F Bond C₂H₅ 1020 n-C₃H₇ H F F F Bond n-C₃H₇ 1021 n-C₃H₇ H F F F Bondn-C₄H₉ 1022 n-C₃H₇ H F F F Bond n-C₅H₁₁ 1023 n-C₃H₇ H F F F Bond n-C₆H₁₃1024 n-C₃H₇ H F F F Bond n-C₇H₁₅ 1025 n-C₃H₇ F F F F Bond CH₃ 1026n-C₃H₇ F F F F Bond C₂H₅ 1027 n-C₃H₇ F F F F Bond n-C₃H₇ 1028 n-C₃H₇ F FF F Bond n-C₄H₉ 1029 n-C₃H₇ F F F F Bond n-C₅H₁₁ 1030 n-C₃H₇ F F F FBond n-C₆H₁₃ 1031 n-C₃H₇ F F F F Bond n-C₇H₁₅ 1032 n-C₄H₉ H H F F BondCH₃ 1033 n-C₄H₉ H H F F Bond C₂H₅ 1034 n-C₄H₉ H H F F Bond n-C₃H₇ 1035n-C₄H₉ H H F F Bond n-C₄H₉ 1036 n-C₄H₉ H H F F Bond n-C₅H₁₁ 1037 n-C₄H₉H H F F Bond n-C₆H₁₃ 1038 n-C₄H₉ H H F F Bond n-C₇H₁₅ 1039 n-C₄H₉ F F FF Bond CH₃ 1040 n-C₄H₉ F F F F Bond C₂H₅ 1041 n-C₄H₉ F F F F Bond n-C₃H₇1042 n-C₄H₉ F F F F Bond n-C₄H₉ 1043 n-C₄H₉ F F F F Bond n-C₅H₁₁ 1044n-C₄H₉ F F F F Bond n-C₆H₁₃ 1045 n-C₄H₉ F F F F Bond n-C₇H₁₅ 1046n-C₅H₁₁ H H F F Bond CH₃ 1047 n-C₅H₁₁ H H F F Bond C₂H₅ 1048 n-C₅H₁₁ H HF F Bond n-C₃H₇ 1049 n-C₅H₁₁ H H F F Bond n-C₄H₉ 1050 n-C₅H₁₁ H H F FBond n-C₅H₁₁ 1051 n-C₅H₁₁ H H F F Bond n-C₆H₁₃ 1052 n-C₅H₁₁ H H F F Bondn-C₇H₁₅ 1053 n-C₅H₁₁ F F F F Bond CH₃ 1054 n-C₅H₁₁ F F F F Bond C₂H₅1055 n-C₅H₁₁ F F F F Bond n-C₃H₇ 1056 n-C₅H₁₁ F F F F Bond n-C₄H₉ 1057n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 1058 n-C₅H₁₁ F F F F Bond n-C₆H₁₃ 1059n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 1060-1206

Example E¹ X^(1a) X^(1b) X² X³ Z R 1060 H H H H F Bond CH₃ 1061 H H H HF Bond C₂H₅ 1062 H H H H F Bond n-C₃H₇ 1063 H H H H F Bond n-C₄H₉ 1064 HH H H F Bond n-C₅H₁₁ 1065 H H H H F Bond n-C₆H₁₃ 1066 H H H H F Bondn-C₇H₁₅ 1067 H H H F F Bond CH₃ 1068 H H H F F Bond C₂H₅ 1069 H H H F FBond n-C₃H₇ 1070 H H H F F Bond n-C₄H₉ 1071 H H H F F Bond n-C₅H₁₁ 1072H H H F F Bond n-C₆H₁₃ 1073 H H H F F Bond n-C₇H₁₅ 1074 H H F F F BondCH₃ 1075 H H F F F Bond C₂H₅ 1076 H H F F F Bond n-C₃H₇ 1077 H H F F FBond n-C₄H₉ 1078 H H F F F Bond n-C₅H₁₁ 1079 H H F F F Bond n-C₆H₁₃ 1080H H F F F Bond n-C₇H₁₅ 1081 H F F F F Bond CH₃ 1082 H F F F F Bond C₂H₅1083 H F F F F Bond n-C₃H₇ 1084 H F F F F Bond n-C₄H₉ 1085 H F F F FBond n-C₅H₁₁ 1086 H F F F F Bond n-C₆H₁₃ 1087 H F F F F Bond n-C₇H₁₅1088 H H F F F CF₂CF₂ CH₃ 1089 H H F F F CF₂CF₂ C₂H₅ 1090 H H F F FCF₂CF₂ n-C₃H₇ 1091 H H F F F CF₂CF₂ n-C₄H₉ 1092 H H F F F CF₂CF₂ n-C₅H₁₁1093 H H F F F CF₂CF₂ n-C₆H₁₃ 1094 H H F F F CF₂CF₂ n-C₇H₁₅ 1095 H F F FF CF₂CF₂ CH₃ 1096 H F F F F CF₂CF₂ C₂H₅ 1097 H F F F F CF₂CF₂ n-C₃H₇1098 H F F F F CF₂CF₂ n-C₄H₉ 1099 H F F F F CF₂CF₂ n-C₅H₁₁ 1100 H F F FF CF₂CF₂ n-C₆H₁₃ 1101 H F F F F CF₂CF₂ n-C₇H₁₅ 1102 H F F F F CF₂O CH₃1103 H F F F F CF₂O C₂H₅ 1104 H F F F F CF₂O n-C₃H₇ 1105 H F F F F CF₂On-C₄H₉ 1106 H F F F F CF₂O n-C₅H₁₁ 1107 H F F F F CF₂O n-C₆H₁₃ 1108 H FF F F CF₂O n-C₇H₁₅ 1109 CH₃ H H F F Bond CH₃ 1110 CH₃ H H F F Bond C₂H₅1111 CH₃ H H F F Bond n-C₃H₇ 1112 CH₃ H H F F Bond n-C₄H₉ 1113 CH₃ H H FF Bond n-C₅H₁₁ 1114 CH₃ H H F F Bond n-C₆H₁₃ 1115 CH₃ H H F F Bondn-C₇H₁₅ 1116 CH₃ H F F F Bond CH₃ 1117 CH₃ H F F F Bond C₂H₅ 1118 CH₃ HF F F Bond n-C₃H₇ 1119 CH₃ H F F F Bond n-C₄H₉ 1120 CH₃ H F F F Bondn-C₅H₁₁ 1121 CH₃ H F F F Bond n-C₆H₁₃ 1122 CH₃ H F F F Bond n-C₇H₁₅ 1123CH₃ F F F F Bond CH₃ 1124 CH₃ F F F F Bond C₂H₅ 1125 CH₃ F F F F Bondn-C₃H₇ 1126 CH₃ F F F F Bond n-C₄H₉ 1127 CH₃ F F F F Bond n-C₅H₁₁ 1128CH₃ F F F F Bond n-C₆H₁₃ 1129 CH₃ F F F F Bond n-C₇H₁₅ 1130 CH₃ F F F FCF₂CF₂ CH₃ 1131 CH₃ F F F F CF₂CF₂ C₂H₅ 1132 CH₃ F F F F CF₂CF₂ n-C₃H₇1133 CH₃ F F F F CF₂CF₂ n-C₄H₉ 1134 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 1135 CH₃F F F F CF₂CF₂ n-C₆H₁₃ 1136 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 1137 CH₃ F F F FCF₂O CH₃ 1138 CH₃ F F F F CF₂O C₂H₅ 1139 CH₃ F F F F CF₂O n-C₃H₇ 1140CH₃ F F F F CF₂O n-C₄H₉ 1141 CH₃ F F F F CF₂O n-C₅H₁₁ 1142 CH₃ F F F FCF₂O n-C₆H₁₃ 1143 CH₃ F F F F CF₂O n-C₇H₁₅ 1144 C₂H₅ H H F F Bond CH₃1145 C₂H₅ H H F F Bond C₂H₅ 1146 C₂H₅ H H F F Bond n-C₃H₇ 1147 C₂H₅ H HF F Bond n-C₄H₉ 1148 C₂H₅ H H F F Bond n-C₅H₁₁ 1149 C₂H₅ H H F F Bondn-C₆H₁₃ 1150 C₂H₅ H H F F Bond n-C₇H₁₅ 1151 C₂H₅ F F F F Bond CH₃ 1152C₂H₅ F F F F Bond C₂H₅ 1153 C₂H₅ F F F F Bond n-C₃H₇ 1154 C₂H₅ F F F FBond n-C₄H₉ 1155 C₂H₅ F F F F Bond n-C₅H₁₁ 1156 C₂H₅ F F F F Bondn-C₆H₁₃ 1157 C₂H₅ F F F F Bond n-C₇H₁₅ 1158 n-C₃H₇ H H F F Bond CH₃ 1159n-C₃H₇ H H F F Bond C₂H₅ 1160 n-C₃H₇ H H F F Bond n-C₃H₇ 1161 n-C₃H₇ H HF F Bond n-C₄H₉ 1162 n-C₃H₇ H H F F Bond n-C₅H₁₁ 1163 n-C₃H₇ H H F FBond n-C₆H₁₃ 1164 n-C₃H₇ H H F F Bond n-C₇H₁₅ 1165 n-C₃H₇ H F F F BondCH₃ 1166 n-C₃H₇ H F F F Bond C₂H₅ 1167 n-C₃H₇ H F F F Bond n-C₃H₇ 1168n-C₃H₇ H F F F Bond n-C₄H₉ 1169 n-C₃H₇ H F F F Bond n-C₅H₁₁ 1170 n-C₃H₇H F F F Bond n-C₆H₁₃ 1171 n-C₃H₇ H F F F Bond n-C₇H₁₅ 1172 n-C₃H₇ F F FF Bond CH₃ 1173 n-C₃H₇ F F F F Bond C₂H₅ 1174 n-C₃H₇ F F F F Bond n-C₃H₇1175 n-C₃H₇ F F F F Bond n-C₄H₉ 1176 n-C₃H₇ F F F F Bond n-C₅H₁₁ 1177n-C₃H₇ F F F F Bond n-C₆H₁₃ 1178 n-C₃H₇ F F F F Bond n-C₇H₁₅ 1179 n-C₄H₉H H F F Bond CH₃ 1180 n-C₄H₉ H H F F Bond C₂H₅ 1181 n-C₄H₉ H H F F Bondn-C₃H₇ 1182 n-C₄H₉ H H F F Bond n-C₄H₉ 1183 n-C₄H₉ H H F F Bond n-C₅H₁₁1184 n-C₄H₉ H H F F Bond n-C₆H₁₃ 1185 n-C₄H₉ H H F F Bond n-C₇H₁₅ 1186n-C₄H₉ F F F F Bond CH₃ 1187 n-C₄H₉ F F F F Bond C₂H₅ 1188 n-C₄H₉ F F FF Bond n-C₃H₇ 1189 n-C₄H₉ F F F F Bond n-C₄H₉ 1190 n-C₄H₉ F F F F Bondn-C₅H₁₁ 1191 n-C₄H₉ F F F F Bond n-C₆H₁₃ 1192 n-C₄H₉ F F F F Bondn-C₇H₁₅ 1193 n-C₅H₁₁ H H F F Bond CH₃ 1194 n-C₅H₁₁ H H F F Bond C₂H₅1195 n-C₅H₁₁ H H F F Bond n-C₃H₇ 1196 n-C₅H₁₁ H H F F Bond n-C₄H₉ 1197n-C₅H₁₁ H H F F Bond n-C₅H₁₁ 1198 n-C₅H₁₁ H H F F Bond n-C₆H₁₃ 1199n-C₅H₁₁ H H F F Bond n-C₇H₁₅ 1200 n-C₅H₁₁ F F F F Bond CH₃ 1201 n-C₅H₁₁F F F F Bond C₂H₅ 1202 n-C₅H₁₁ F F F F Bond n-C₃H₇ 1203 n-C₅H₁₁ F F F FBond n-C₄H₉ 1204 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 1205 n-C₅H₁₁ F F F F Bondn-C₆H₁₃ 1206 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 1207-1304

Example R^(b) X^(1a) X^(1b) X² X³ Z R 1207 CH₃ H H F F Bond CH₃ 1208 CH₃H H F F Bond C₂H₅ 1209 CH₃ H H F F Bond n-C₃H₇ 1210 CH₃ H H F F Bondn-C₄H₉ 1211 CH₃ H H F F Bond n-C₅H₁₁ 1212 CH₃ H H F F Bond n-C₆H₁₃ 1213CH₃ H H F F Bond n-C₇H₁₅ 1214 CH₃ H F F F Bond CH₃ 1215 CH₃ H F F F BondC₂H₅ 1216 CH₃ H F F F Bond n-C₃H₇ 1217 CH₃ H F F F Bond n-C₄H₉ 1218 CH₃H F F F Bond n-C₅H₁₁ 1219 CH₃ H F F F Bond n-C₆H₁₃ 1220 CH₃ H F F F Bondn-C₇H₁₅ 1221 CH₃ F F F F Bond CH₃ 1222 CH₃ F F F F Bond C₂H₅ 1223 CH₃ FF F F Bond n-C₃H₇ 1224 CH₃ F F F F Bond n-C₄H₉ 1225 CH₃ F F F F Bondn-C₅H₁₁ 1226 CH₃ F F F F Bond n-C₆H₁₃ 1227 CH₃ F F F F Bond n-C₇H₁₅ 1228CH₃ H F F F CF₂CF₂ CH₃ 1229 CH₃ H F F F CF₂CF₂ C₂H₅ 1230 CH₃ H F F FCF₂CF₂ n-C₃H₇ 1231 CH₃ H F F F CF₂CF₂ n-C₄H₉ 1232 CH₃ H F F F CF₂CF₂n-C₅H₁₁ 1233 CH₃ H F F F CF₂CF₂ n-C₆H₁₃ 1234 CH₃ H F F F CF₂CF₂ n-C₇H₁₅1235 CH₃ F F F F CF₂CF₂ CH₃ 1236 CH₃ F F F F CF₂CF₂ C₂H₅ 1237 CH₃ F F FF CF₂CF₂ n-C₃H₇ 1238 CH₃ F F F F CF₂CF₂ n-C₄H₉ 1239 CH₃ F F F F CF₂CF₂n-C₅H₁₁ 1240 CH₃ F F F F CF₂CF₂ n-C₆H₁₃ 1241 CH₃ F F F F CF₂CF₂ n-C₇H₁₅1242 C₂H₅ H H F F Bond CH₃ 1243 C₂H₅ H H F F Bond C₂H₅ 1244 C₂H₅ H H F FBond n-C₃H₇ 1245 C₂H₅ H H F F Bond n-C₄H₉ 1246 C₂H₅ H H F F Bond n-C₅H₁₁1247 C₂H₅ H H F F Bond n-C₆H₁₃ 1248 C₂H₅ H H F F Bond n-C₇H₁₅ 1249 C₂H₅F F F F CF₂CF₂ CH₃ 1250 C₂H₅ F F F F CF₂CF₂ C₂H₅ 1251 C₂H₅ F F F FCF₂CF₂ n-C₃H₇ 1252 C₂H₅ F F F F CF₂CF₂ n-C₄H₉ 1253 C₂H₅ F F F F CF₂CF₂n-C₅H₁₁ 1254 C₂H₅ F F F F CF₂CF₂ n-C₆H₁₃ 1255 C₂H₅ F F F F CF₂CF₂n-C₇H₁₅ 1256 C₂H₅ F F F F Bond CH₃ 1257 C₂H₅ F F F F Bond C₂H₅ 1258 C₂H₅F F F F Bond n-C₃H₇ 1259 C₂H₅ F F F F Bond n-C₄H₉ 1260 C₂H₅ F F F F Bondn-C₅H₁₁ 1261 C₂H₅ F F F F Bond n-C₆H₁₃ 1262 C₂H₅ F F F F Bond n-C₇H₁₅1263 n-C₃H₇ H H F F Bond CH₃ 1264 n-C₃H₇ H H F F Bond C₂H₅ 1265 n-C₃H₇ HH F F Bond n-C₃H₇ 1266 n-C₃H₇ H H F F Bond n-C₄H₉ 1267 n-C₃H₇ H H F FBond n-C₅H₁₁ 1268 n-C₃H₇ H H F F Bond n-C₆H₁₃ 1269 n-C₃H₇ H H F F Bondn-C₇H₁₅ 1270 n-C₃H₇ F F F F Bond CH₃ 1271 n-C₃H₇ F F F F Bond C₂H₅ 1272n-C₃H₇ F F F F Bond n-C₃H₇ 1273 n-C₃H₇ F F F F Bond n-C₄H₉ 1274 n-C₃H₇ FF F F Bond n-C₅H₁₁ 1275 n-C₃H₇ F F F F Bond n-C₆H₁₃ 1276 n-C₃H₇ F F F FBond n-C₇H₁₅ 1277 n-C₄H₉ H H F F Bond CH₃ 1278 n-C₄H₉ H H F F Bond C₂H₅1279 n-C₄H₉ H H F F Bond n-C₃H₇ 1280 n-C₄H₉ H H F F Bond n-C₄H₉ 1281n-C₄H₉ H H F F Bond n-C₅H₁₁ 1282 n-C₄H₉ H H F F Bond n-C₆H₁₃ 1283 n-C₄H₉H H F F Bond n-C₇H₁₅ 1284 n-C₄H₉ F F F F Bond CH₃ 1285 n-C₄H₉ F F F FBond C₂H₅ 1286 n-C₄H₉ F F F F Bond n-C₃H₇ 1287 n-C₄H₉ F F F F Bondn-C₄H₉ 1288 n-C₄H₉ F F F F Bond n-C₅H₁₁ 1289 n-C₄H₉ F F F F Bond n-C₆H₁₃1290 n-C₄H₉ F F F F Bond n-C₇H₁₅ 1291 n-C₅H₁₁ H H F F Bond CH₃ 1292n-C₅H₁₁ H H F F Bond C₂H₅ 1293 n-C₅H₁₁ H H F F Bond n-C₃H₇ 1294 n-C₅H₁₁H H F F Bond n-C₄H₉ 1295 n-C₅H₁₁ H H F F Bond n-C₅H₁₁ 1296 n-C₅H₁₁ H H FF Bond n-C₆H₁₃ 1297 n-C₅H₁₁ H H F F Bond n-C₇H₁₅ 1298 n-C₅H₁₁ F F F FBond CH₃ 1299 n-C₅H₁₁ F F F F Bond C₂H₅ 1300 n-C₅H₁₁ F F F F Bond n-C₃H₇1301 n-C₅H₁₁ F F F F Bond n-C₄H₉ 1302 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 1303n-C₅H₁₁ F F F F Bond n-C₆H₁₃ 1304 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 1305-1423

Example R^(b) X^(1a) X^(1b) X² X³ Z R^(a) 1305 CH₃ H H F F Bond CH₃ 1306CH₃ H H F F Bond C₂H₅ 1307 CH₃ H H F F Bond n-C₃H₇ 1308 CH₃ H H F F Bondn-C₄H₉ 1309 CH₃ H H F F Bond n-C₅H₁₁ 1310 CH₃ H H F F Bond n-C₆H₁₃ 1311CH₃ H H F F Bond n-C₇H₁₅ 1312 CH₃ H F F F Bond CH₃ 1313 CH₃ H F F F BondC₂H₅ 1314 CH₃ H F F F Bond n-C₃H₇ 1315 CH₃ H F F F Bond n-C₄H₉ 1316 CH₃H F F F Bond n-C₅H₁₁ 1317 CH₃ H F F F Bond n-C₆H₁₃ 1318 CH₃ H F F F Bondn-C₇H₁₅ 1319 CH₃ F F F F Bond CH₃ 1320 CH₃ F F F F Bond C₂H₅ 1321 CH₃ FF F F Bond n-C₃H₇ 1322 CH₃ F F F F Bond n-C₄H₉ 1323 CH₃ F F F F Bondn-C₅H₁₁ 1324 CH₃ F F F F Bond n-C₆H₁₃ 1325 CH₃ F F F F Bond n-C₇H₁₅ 1326CH₃ H F F F CF₂CF₂ CH₃ 1327 CH₃ H F F F CF₂CF₂ C₂H₅ 1328 CH₃ H F F FCF₂CF₂ n-C₃H₇ 1329 CH₃ H F F F CF₂CF₂ n-C₄H₉ 1330 CH₃ H F F F CF₂CF₂n-C₅H₁₁ 1331 CH₃ H F F F CF₂CF₂ n-C₆H₁₃ 1332 CH₃ H F F F CF₂CF₂ n-C₇H₁₅1333 CH₃ F F F F CF₂CF₂ CH₃ 1334 CH₃ F F F F CF₂CF₂ C₂H₅ 1335 CH₃ F F FF CF₂CF₂ n-C₃H₇ 1336 CH₃ F F F F CF₂CF₂ n-C₄H₉ 1337 CH₃ F F F F CF₂CF₂n-C₅H₁₁ 1338 CH₃ F F F F CF₂CF₂ n-C₆H₁₃ 1339 CH₃ F F F F CF₂CF₂ n-C₇H₁₅1340 CH₃ H F F F OCF₂ CH₃ 1341 CH₃ H F F F OCF₂ C₂H₅ 1342 CH₃ H F F FOCF₂ n-C₃H₇ 1343 CH₃ H F F F OCF₂ n-C₄H₉ 1344 CH₃ H F F F OCF₂ n-C₅H₁₁1345 CH₃ H F F F OCF₂ n-C₆H₁₃ 1346 CH₃ H F F F OCF₂ n-C₇H₁₅ 1347 CH₃ F FF F OCF₂ CH₃ 1348 CH₃ F F F F OCF₂ C₂H₅ 1349 CH₃ F F F F OCF₂ n-C₃H₇1350 CH₃ F F F F OCF₂ n-C₄H₉ 1351 CH₃ F F F F OCF₂ n-C₅H₁₁ 1352 CH₃ F FF F OCF₂ n-C₆H₁₃ 1353 CH₃ F F F F OCF₂ n-C₇H₁₅ 1354 C₂H₅ H H F F BondCH₃ 1355 C₂H₅ H H F F Bond C₂H₅ 1356 C₂H₅ H H F F Bond n-C₃H₇ 1357 C₂H₅H H F F Bond n-C₄H₉ 1358 C₂H₅ H H F F Bond n-C₅H₁₁ 1359 C₂H₅ H H F FBond n-C₆H₁₃ 1360 C₂H₅ H H F F Bond n-C₇H₁₅ 1361 C₂H₅ F F F F CF₂CF₂ CH₃1362 C₂H₅ F F F F CF₂CF₂ C₂H₅ 1363 C₂H₅ F F F F CF₂CF₂ n-C₃H₇ 1364 C₂H₅F F F F CF₂CF₂ n-C₄H₉ 1365 C₂H₅ F F F F CF₂CF₂ n-C₅H₁₁ 1366 C₂H₅ F F F FCF₂CF₂ n-C₆H₁₃ 1367 C₂H₅ F F F F CF₂CF₂ n-C₇H₁₅ 1368 C₂H₅ F F F F OCF₂CH₃ 1369 C₂H₅ F F F F OCF₂ C₂H₅ 1370 C₂H₅ F F F F OCF₂ n-C₃H₇ 1371 C₂H₅F F F F OCF₂ n-C₄H₉ 1372 C₂H₅ F F F F OCF₂ n-C₅H₁₁ 1373 C₂H₅ F F F FOCF₂ n-C₆H₁₃ 1374 C₂H₅ F F F F OCF₂ n-C₇H₁₅ 1375 C₂H₅ F F F F Bond CH₃1376 C₂H₅ F F F F Bond C₂H₅ 1377 C₂H₅ F F F F Bond n-C₃H₇ 1378 C₂H₅ F FF F Bond n-C₄H₉ 1379 C₂H₅ F F F F Bond n-C₅H₁₁ 1380 C₂H₅ F F F F Bondn-C₆H₁₃ 1381 C₂H₅ F F F F Bond n-C₇H₁₅ 1382 n-C₃H₇ H H F F Bond CH₃ 1383n-C₃H₇ H H F F Bond C₂H₅ 1384 n-C₃H₇ H H F F Bond n-C₃H₇ 1385 n-C₃H₇ H HF F Bond n-C₄H₉ 1386 n-C₃H₇ H H F F Bond n-C₅H₁₁ 1387 n-C₃H₇ H H F FBond n-C₆H₁₃ 1388 n-C₃H₇ H H F F Bond n-C₇H₁₅ 1389 n-C₃H₇ F F F F BondCH₃ 1390 n-C₃H₇ F F F F Bond C₂H₅ 1391 n-C₃H₇ F F F F Bond n-C₃H₇ 1392n-C₃H₇ F F F F Bond n-C₄H₉ 1393 n-C₃H₇ F F F F Bond n-C₅H₁₁ 1394 n-C₃H₇F F F F Bond n-C₆H₁₃ 1395 n-C₃H₇ F F F F Bond n-C₇H₁₅ 1396 n-C₄H₉ H H FF Bond CH₃ 1397 n-C₄H₉ H H F F Bond C₂H₅ 1398 n-C₄H₉ H H F F Bond n-C₃H₇1399 n-C₄H₉ H H F F Bond n-C₄H₉ 1400 n-C₄H₉ H H F F Bond n-C₅H₁₁ 1401n-C₄H₉ H H F F Bond n-C₆H₁₃ 1402 n-C₄H₉ H H F F Bond n-C₇H₁₅ 1403 n-C₄H₉F F F F Bond CH₃ 1404 n-C₄H₉ F F F F Bond C₂H₅ 1405 n-C₄H₉ F F F F Bondn-C₃H₇ 1406 n-C₄H₉ F F F F Bond n-C₄H₉ 1407 n-C₄H₉ F F F F Bond n-C₅H₁₁1408 n-C₄H₉ F F F F Bond n-C₆H₁₃ 1409 n-C₄H₉ F F F F Bond n-C₇H₁₅ 1410n-C₅H₁₁ H H F F Bond CH₃ 1411 n-C₅H₁₁ H H F F Bond C₂H₅ 1412 n-C₅H₁₁ H HF F Bond n-C₃H₇ 1413 n-C₅H₁₁ H H F F Bond n-C₄H₉ 1414 n-C₅H₁₁ H H F FBond n-C₅H₁₁ 1415 n-C₅H₁₁ H H F F Bond n-C₆H₁₃ 1416 n-C₅H₁₁ H H F F Bondn-C₇H₁₅ 1417 n-C₅H₁₁ F F F F Bond CH₃ 1418 n-C₅H₁₁ F F F F Bond C₂H₅1419 n-C₅H₁₁ F F F F Bond n-C₃H₇ 1420 n-C₅H₁₁ F F F F Bond n-C₄H₉ 1421n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 1422 n-C₅H₁₁ F F F F Bond n-C₆H₁₃ 1423n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 1424-1507

Example E¹ X¹ X² X³ R 1424 H H F F CH₃ 1425 H H F F C₂H₅ 1426 H H F Fn-C₃H₇ 1427 H H F F n-C₄H₉ 1428 H H F F n-C₅H₁₁ 1429 H H F F n-C₆H₁₃1430 H H F F n-C₇H₁₅ 1431 H F F F CH₃ 1432 H F F F C₂H₅ 1433 H F F Fn-C₃H₇ 1434 H F F F n-C₄H₉ 1435 H F F F n-C₅H₁₁ 1436 H F F F n-C₆H₁₃1437 H F F F n-C₇H₁₅ 1438 CH₃ H F F CH₃ 1439 CH₃ H F F C₂H₅ 1440 CH₃ H FF n-C₃H₇ 1441 CH₃ H F F n-C₄H₉ 1442 CH₃ H F F n-O5H11 1443 CH₃ H F Fn-C₆H₁₃ 1444 CH₃ H F F n-C₇H₁₅ 1445 CH₃ F F F CH₃ 1446 CH₃ F F F C₂H₅1447 CH₃ F F F n-C₃H₇ 1448 CH₃ F F F n-C₄H₉ 1449 CH₃ F F F n-C₅H₁₁ 1450CH₃ F F F n-C₆H₁₃ 1451 CH₃ F F F n-C₇H₁₅ 1452 C₂H₅ H F F CH₃ 1453 C₂H₅ HF F C₂H₅ 1454 C₂H₅ H F F n-C₃H₇ 1455 C₂H₅ H F F n-C₄H₉ 1456 C₂H₅ H F Fn-C₅H₁₁ 1457 C₂H₅ H F F n-C₆H₁₃ 1458 C₂H₅ H F F n-C₇H₁₅ 1459 C₂H₅ F F FCH₃ 1460 C₂H₅ F F F C₂H₅ 1461 C₂H₅ F F F n-C₃H₇ 1462 C₂H₅ F F F n-C₄H₉1463 C₂H₅ F F F n-C₅H₁₁ 1464 C₂H₅ F F F n-C₆H₁₃ 1465 C₂H₅ F F F n-C₇H₁₅1466 n-C₃H₇ H F F CH₃ 1467 n-C₃H₇ H F F C₂H₅ 1468 n-C₃H₇ H F F n-C₃H₇1469 n-C₃H₇ H F F n-C₄H₉ 1470 n-C₃H₇ H F F n-C₅H₁₁ 1471 n-C₃H₇ H F Fn-C₆H₁₃ 1472 n-C₃H₇ H F F n-C₇H₁₅ 1473 n-C₃H₇ F F F CH₃ 1474 n-C₃H₇ F FF C₂H₅ 1475 n-C₃H₇ F F F n-C₃H₇ 1476 n-C₃H₇ F F F n-C₄H₉ 1477 n-C₃H₇ F FF n-C₅H₁₁ 1478 n-C₃H₇ F F F n-C₆H₁₃ 1479 n-C₃H₇ F F F n-C₇H₁₅ 1480n-C₄H₉ H F F CH₃ 1481 n-C₄H₉ H F F C₂H₅ 1482 n-C₄H₉ H F F n-C₃H₇ 1483n-C₄H₉ H F F n-C₄H₉ 1484 n-C₄H₉ H F F n-C₅H₁₁ 1485 n-C₄H₉ H F F n-C₆H₁₃1486 n-C₄H₉ H F F n-C₇H₁₅ 1487 n-C₄H₉ F F F CH₃ 1488 n-C₄H₉ F F F C₂H₅1489 n-C₄H₉ F F F n-C₃H₇ 1490 n-C₄H₉ F F F n-C₄H₉ 1491 n-C₄H₉ F F Fn-C₅H₁₁ 1492 n-C₄H₉ F F F n-C₆H₁₃ 1493 n-C₄H₉ F F F n-C₇H₁₅ 1494 n-C₅H₁₁H F F CH₃ 1495 n-C₅H₁₁ H F F C₂H₅ 1496 n-C₅H₁₁ H F F n-C₃H₇ 1497 n-C₅H₁₁H F F n-C₄H₉ 1498 n-C₅H₁₁ H F F n-C₅H₁₁ 1499 n-C₅H₁₁ H F F n-C₆H₁₃ 1500n-C₅H₁₁ H F F n-C₇H₁₅ 1501 n-C₅H₁₁ F F F CH₃ 1502 n-C₅H₁₁ F F F C₂H₅1503 n-C₅H₁₁ F F F n-C₃H₇ 1504 n-C₅H₁₁ F F F n-C₄H₉ 1505 n-C₅H₁₁ F F Fn-C₅H₁₁ 1506 n-C₅H₁₁ F F F n-C₆H₁₃ 1507 n-C₅H₁₁ F F F n-C₇H₁₅

Examples 1508-1577

Example E¹ X¹ X² X³ Z R 1508 H F F F Bond CH₃ 1509 H F F F Bond C₂H₅1510 H F F F Bond n-C₃H₇ 1511 H F F F Bond n-C₄H₉ 1512 H F F F Bondn-C₅H₁₁ 1513 H F F F Bond n-C₆H₁₃ 1514 H F F F Bond n-C₇H₁₅ 1515 H F F FCF₂CF₂ CH₃ 1516 H F F F CF₂CF₂ C₂H₅ 1517 H F F F CF₂CF₂ n-C₃H₇ 1518 H FF F CF₂CF₂ n-C₄H₉ 1519 H F F F CF₂CF₂ n-C₅H₁₁ 1520 H F F F CF₂CF₂n-C₆H₁₃ 1521 H F F F CF₂CF₂ n-C₇H₁₅ 1522 H F F F OCF₂ CH₃ 1523 H F F FOCF₂ C₂H₅ 1524 H F F F OCF₂ n-C₃H₇ 1525 H F F F OCF₂ n-C₄H₉ 1526 H F F FOCF₂ n-C₅H₁₁ 1527 H F F F OCF₂ n-C₆H₁₃ 1528 H F F F OCF₂ n-C₇H₁₅ 1529CH₃ F F F Bond CH₃ 1530 CH₃ F F F Bond C₂H₅ 1531 CH₃ F F F Bond n-C₃H₇1532 CH₃ F F F Bond n-C₄H₉ 1533 CH₃ F F F Bond n-C₅H₁₁ 1534 CH₃ F F FBond n-C₆H₁₃ 1535 CH₃ F F F Bond n-C₇H₁₅ 1536 CH₃ F F F CF₂CF₂ CH₃ 1537CH₃ F F F CF₂CF₂ C₂H₅ 1538 CH₃ F F F CF₂CF₂ n-C₃H₇ 1539 CH₃ F F F CF₂CF₂n-C₄H₉ 1540 CH₃ F F F CF₂CF₂ n-C₅H₁₁ 1541 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 1542CH₃ F F F CF₂CF₂ n-C₇H₁₅ 1543 CH₃ F F F OCF₂ CH₃ 1544 CH₃ F F F OCF₂C₂H₅ 1545 CH₃ F F F OCF₂ n-C₃H₇ 1546 CH₃ F F F OCF₂ n-C₄H₉ 1547 CH₃ F FF OCF₂ n-C₅H₁₁ 1548 CH₃ F F F OCF₂ n-C₆H₁₃ 1549 CH₃ F F F OCF₂ n-C₇H₁₅1550 C₂H₅ F F F Bond CH₃ 1551 C₂H₅ F F F Bond C₂H₅ 1552 C₂H₅ F F F Bondn-C₃H₇ 1553 C₂H₅ F F F Bond n-C₄H₉ 1554 C₂H₅ F F F Bond n-C₅H₁₁ 1555C₂H₅ F F F Bond n-C₆H₁₃ 1556 C₂H₅ F F F Bond n-C₇H₁₅ 1557 n-C₃H₇ F F FBond CH₃ 1558 n-C₃H₇ F F F Bond C₂H₅ 1559 n-C₃H₇ F F F Bond n-C₃H₇ 1560n-C₃H₇ F F F Bond n-C₄H₉ 1561 n-C₃H₇ F F F Bond n-C₅H₁₁ 1562 n-C₃H₇ F FF Bond n-C₆H₁₃ 1563 n-C₃H₇ F F F Bond n-C₇H₁₅ 1564 n-C₄H₉ F F F Bond CH₃1565 n-C₄H₉ F F F Bond C₂H₅ 1566 n-C₄H₉ F F F Bond n-C₃H₇ 1567 n-C₄H₉ FF F Bond n-C₄H₉ 1568 n-C₄H₉ F F F Bond n-C₅H₁₁ 1569 n-C₄H₉ F F F Bondn-C₆H₁₃ 1570 n-C₄H₉ F F F Bond n-C₇H₁₅ 1571 n-C₄H₁₁ F F F Bond CH₃ 1572n-C₅H₁₁ F F F Bond C₂H₅ 1573 n-C₅H₁₁ F F F Bond n-C₃H₇ 1574 n-C₅H₁₁ F FF Bond n-C₄H₉ 1575 n-C₅H₁₁ F F F Bond n-C₅H₁₁ 1576 n-C₅H₁₁ F F F Bondn-C₆H₁₃ 1577 n-C₅H₁₁ F F F Bond n-C₇H₁₅

Examples 1578-1647

Example E¹ X¹ X² X³ Z R 1578 H F F F Bond CH₃ 1579 H F F F Bond C₂H₅1580 H F F F Bond n-C₃H₇ 1581 H F F F Bond n-C₄H₉ 1582 H F F F Bondn-C₅H₁₁ 1583 H F F F Bond n-C₆H₁₃ 1584 H F F F Bond n-C₇H₁₅ 1585 H F F FCF₂CF₂ CH₃ 1586 H F F F CF₂CF₂ C₂H₅ 1587 H F F F CF₂CF₂ n-C₃H₇ 1588 H FF F CF₂CF₂ n-C₄H₉ 1589 H F F F CF₂CF₂ n-C₅H₁₁ 1590 H F F F CF₂CF₂n-C₆H₁₃ 1591 H F F F CF₂CF₂ n-C₇H₁₅ 1592 H F F F CF₂O CH₃ 1593 H F F FCF₂O C₂H₅ 1594 H F F F CF₂O n-C₃H₇ 1595 H F F F CF₂O n-C₄H₉ 1596 H F F FCF₂O n-C₅H₁₁ 1597 H F F F CF₂O n-C₆H₁₃ 1598 H F F F CF₂O n-C₇H₁₅ 1599CH₃ F F F Bond CH₃ 1600 CH₃ F F F Bond C₂H₅ 1601 CH₃ F F F Bond n-C₃H₇1602 CH₃ F F F Bond n-C₄H₉ 1603 CH₃ F F F Bond n-C₅H₁₁ 1604 CH₃ F F FBond n-C₆H₁₃ 1605 CH₃ F F F Bond n-C₇H₁₅ 1606 CH₃ F F F CF₂CF₂ CH₃ 1607CH₃ F F F CF₂CF₂ C₂H₅ 1608 CH₃ F F F CF₂CF₂ n-C₃H₇ 1609 CH₃ F F F CF₂CF₂n-C₄H₉ 1610 CH₃ F F F CF₂CF₂ n-C₅H₁₁ 1611 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 1612CH₃ F F F CF₂CF₂ n-C₇H₁₅ 1613 CH₃ F F F CF₂O CH₃ 1614 CH₃ F F F CF₂OC₂H₅ 1615 CH₃ F F F CF₂O n-C₃H₇ 1616 CH₃ F F F CF₂O n-C₄H₉ 1617 CH₃ F FF CF₂O n-C₅H₁₁ 1618 CH₃ F F F CF₂O n-C₆H₁₃ 1619 CH₃ F F F CF₂O n-C₇H₁₅1620 C₂H₅ F F F Bond CH₃ 1621 C₂H₅ F F F Bond C₂H₅ 1622 C₂H₅ F F F Bondn-C₃H₇ 1623 C₂H₅ F F F Bond n-C₄H₉ 1624 C₂H₅ F F F Bond n-C₅H₁₁ 1625C₂H₅ F F F Bond n-C₆H₁₃ 1626 C₂H₅ F F F Bond n-C₇H₁₅ 1627 n-C₃H₇ F F FBond CH₃ 1628 n-C₃H₇ F F F Bond C₂H₅ 1629 n-C₃H₇ F F F Bond n-C₃H₇ 1630n-C₃H₇ F F F Bond n-C₄H₉ 1631 n-C₃H₇ F F F Bond n-C₅H₁₁ 1632 n-C₃H₇ F FF Bond n-C₆H₁₃ 1633 n-C₃H₇ F F F Bond n-C₇H₁₅ 1634 n-C₄H₉ F F F Bond CH₃1635 n-C₄H₉ F F F Bond C₂H₅ 1636 n-C₄H₉ F F F Bond n-C₃H₇ 1637 n-C₄H₉ FF F Bond n-C₄H₉ 1638 n-C₄H₉ F F F Bond n-C₅H₁₁ 1639 n-C₄H₉ F F F Bondn-C₆H₁₃ 1640 n-C₄H₉ F F F Bond n-C₇H₁₅ 1641 n-C₅H₁₁ F F F Bond CH₃ 1642n-C₅H₁₁ F F F Bond C₂H₅ 1643 n-C₅H₁₁ F F F Bond n-C₃H₇ 1644 n-C₅H₁₁ F FF Bond n-C₄H₉ 1645 n-C₅H₁₁ F F F Bond n-C₅H₁₁ 1646 n-C₅H₁₁ F F F Bondn-C₆H₁₃ 1647 n-C₅H₁₁ F F F Bond n-C₇H₁₅

Examples 1648-1717

Example E¹ X¹ X² X³ Z R 1648 H F F F Bond CH₃ 1649 H F F F Bond C₂H₅1650 H F F F Bond n-C₃H₇ 1651 H F F F Bond n-C₄H₉ 1652 H F F F Bondn-C₅H₁₁ 1653 H F F F Bond n-C₆H₁₃ 1654 H F F F Bond n-C₇H₁₅ 1655 H F F FCF₂CF₂ CH₃ 1656 H F F F CF₂CF₂ C₂H₅ 1657 H F F F CF₂CF₂ n-C₃H₇ 1658 H FF F CF₂CF₂ n-C₄H₉ 1659 H F F F CF₂CF₂ n-C₅H₁₁ 1660 H F F F CF₂CF₂n-C₆H₁₃ 1661 H F F F CF₂CF₂ n-C₇H₁₅ 1662 H F F F CF₂O CH₃ 1663 H F F FCF₂O C₂H₅ 1664 H F F F CF₂O n-C₃H₇ 1665 H F F F CF₂O n-C₄H₉ 1666 H F F FCF₂O n-C₅H₁₁ 1667 H F F F CF₂O n-C₆H₁₃ 1668 H F F F CF₂O n-C₇H₁₅ 1669CH₃ F F F Bond CH₃ 1670 CH₃ F F F Bond C₂H₅ 1671 CH₃ F F F Bond n-C₃H₇1672 CH₃ F F F Bond n-C₄H₉ 1673 CH₃ F F F Bond n-C₅H₁₁ 1674 CH₃ F F FBond n-C₆H₁₃ 1675 CH₃ F F F Bond n-C₇H₁₅ 1676 CH₃ F F F CF₂CF₂ CH₃ 1677CH₃ F F F CF₂CF₂ C₂H₅ 1678 CH₃ F F F CF₂CF₂ n-C₃H₇ 1679 CH₃ F F F CF₂CF₂n-C₄H₉ 1680 CH₃ F F F CF₂CF₂ n-C₅H₁₁ 1681 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 1682CH₃ F F F CF₂CF₂ n-C₇H₁₅ 1683 CH₃ F F F CF₂O CH₃ 1684 CH₃ F F F CF₂OC₂H₅ 1685 CH₃ F F F CF₂O n-C₃H₇ 1686 CH₃ F F F CF₂O n-C₄H₉ 1687 CH₃ F FF CF₂O n-C₅H₁₁ 1688 CH₃ F F F CF₂O n-C₆H₁₃ 1689 CH₃ F F F CF₂O n-C₇H₁₅1690 C₂H₅ F F F Bond CH₃ 1691 C₂H₅ F F F Bond C₂H₅ 1692 C₂H₅ F F F Bondn-C₃H₇ 1693 C₂H₅ F F F Bond n-C₄H₉ 1694 C₂H₅ F F F Bond n-C₅H₁₁ 1695C₂H₅ F F F Bond n-C₆H₁₃ 1696 C₂H₅ F F F Bond n-C₇H₁₅ 1697 n-C₃H₇ F F FBond CH₃ 1698 n-C₃H₇ F F F Bond C₂H₅ 1699 n-C₃H₇ F F F Bond n-C₃H₇ 1700n-C₃H₇ F F F Bond n-C₄H₉ 1701 n-C₃H₇ F F F Bond n-C₅H₁₁ 1702 n-C₃H₇ F FF Bond n-C₆H₁₃ 1703 n-C₃H₇ F F F Bond n-C₇H₁₅ 1704 n-C₄H₉ F F F Bond CH₃1705 n-C₄H₉ F F F Bond C₂H₅ 1706 n-C₄H₉ F F F Bond n-C₃H₇ 1707 n-C₄H₉ FF F Bond n-C₄H₉ 1708 n-C₄H₉ F F F Bond n-C₅H₁₁ 1709 n-C₄H₉ F F F Bondn-C₆H₁₃ 1710 n-C₄H₉ F F F Bond n-C₇H₁₅ 1711 n-C₅H₁₁ F F F Bond CH₃ 1712n-C₅H₁₁ F F F Bond C₂H₅ 1713 n-C₅H₁₁ F F F Bond n-C₃H₇ 1714 n-C₅H₁₁ F FF Bond n-C₄H₉ 1715 n-C₅H₁₁ F F F Bond n-C₅H₁₁ 1716 n-C₅H₁₁ F F F Bondn-C₆H₁₃ 1717 n-C₅H₁₁ F F F Bond n-C₇H₁₅

Examples 1718-1766

Example R^(b) X¹ X² X³ Z R^(a) 1718 CH₃ F F F Bond CH₃ 1719 CH₃ F F FBond C₂H₅ 1720 CH₃ F F F Bond n-C₃H₇ 1721 CH₃ F F F Bond n-C₄H₉ 1722 CH₃F F F Bond n-C₅H₁₁ 1723 CH₃ F F F Bond n-C₆H₁₃ 1724 CH₃ F F F Bondn-C₇H₁₅ 1725 CH₃ F F F CF₂CF₂ CH₃ 1726 CH₃ F F F CF₂CF₂ C₂H₅ 1727 CH₃ FF F CF₂CF₂ n-C₃H₇ 1728 CH₃ F F F CF₂CF₂ n-C₄H₉ 1729 CH₃ F F F CF₂CF₂n-C₅H₁₁ 1730 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 1731 CH₃ F F F CF₂CF₂ n-C₇H₁₅ 1732C₂H₅ F F F CF₂CF₂ CH₃ 1733 C₂H₅ F F F CF₂CF₂ C₂H₅ 1734 C₂H₅ F F F CF₂CF₂n-C₃H₇ 1735 C₂H₅ F F F CF₂CF₂ n-C₄H₉ 1736 C₂H₅ F F F CF₂CF₂ n-C₅H₁₁ 1737C₂H₅ F F F CF₂CF₂ n-C₆H₁₃ 1738 C₂H₅ F F F CF₂CF₂ n-C₇H₁₅ 1739 C₂H₅ F F FBond CH₃ 1740 C₂H₅ F F F Bond C₂H₅ 1741 C₂H₅ F F F Bond n-C₃H₇ 1742 C₂H₅F F F Bond n-C₄H₉ 1743 C₂H₅ F F F Bond n-C₅H₁₁ 1744 C₂H₅ F F F Bondn-C₆H₁₃ 1745 C₂H₅ F F F Bond n-C₇H₁₅ 1746 n-C₃H₇ F F F Bond CH₃ 1747n-C₃H₇ F F F Bond C₂H₅ 1748 n-C₃H₇ F F F Bond n-C₃H₇ 1749 n-C₃H₇ F F FBond n-C₄H₉ 1750 n-C₃H₇ F F F Bond n-C₅H₁₁ 1751 n-C₃H₇ F F F Bondn-C₆H₁₃ 1752 n-C₃H₇ F F F Bond n-C₇H₁₅ 1753 n-C₄H₉ F F F Bond CH₃ 1754n-C₄H₉ F F F Bond C₂H₅ 1755 n-C₄H₉ F F F Bond n-C₃H₇ 1756 n-C₄H₉ F F FBond n-C₄H₉ 1757 n-C₄H₉ F F F Bond n-C₅H₁₁ 1758 n-C₄H₉ F F F Bondn-C₆H₁₃ 1759 n-C₄H₉ F F F Bond n-C₇H₁₅ 1760 n-C₅H₁₁ F F F Bond CH₃ 1761n-C₅H₁₁ F F F Bond C₂H₅ 1762 n-C₅H₁₁ F F F Bond n-C₃H₇ 1763 n-C₅H₁₁ F FF Bond n-C₄H₉ 1764 n-C₅H₁₁ F F F Bond n-C₅H₁₁ 1765 n-C₅H₁₁ F F F Bondn-C₆H₁₃ 1766 n-C₅H₁₁ F F F Bond n-C₇H₁₅

Examples 1767-1829

Example R^(b) X¹ X² X³ Z R^(a) 1767 CH₃ F F F Bond CH₃ 1768 CH₃ F F FBond C₂H₅ 1769 CH₃ F F F Bond n-C₃H₇ 1770 CH₃ F F F Bond n-C₄H₉ 1771 CH₃F F F Bond n-C₅H₁₁ 1772 CH₃ F F F Bond n-C₆H₁₃ 1773 CH₃ F F F Bondn-C₇H₁₅ 1774 CH₃ F F F CF₂CF₂ CH₃ 1775 CH₃ F F F CF₂CF₂ C₂H₅ 1776 CH₃ FF F CF₂CF₂ n-C₃H₇ 1777 CH₃ F F F CF₂CF₂ n-C₄H₉ 1778 CH₃ F F F CF₂CF₂n-C₅H₁₁ 1779 CH₃ F F F CF₂CF₂ n-C₆H₁₃ 1780 CH₃ F F F CF₂CF₂ n-C₇H₁₅ 1781CH₃ F F F CF₂O CH₃ 1782 CH₃ F F F CF₂O C₂H₅ 1783 CH₃ F F F CF₂O n-C₃H₇1784 CH₃ F F F CF₂O n-C₄H₉ 1785 CH₃ F F F CF₂O n-C₅H₁₁ 1786 CH₃ F F FCF₂O n-C₆H₁₃ 1787 CH₃ F F F CF₂O n-C₇H₁₅ 1788 C₂H₅ F F F CF₂CF₂ CH₃ 1789C₂H₅ F F F CF₂CF₂ C₂H₅ 1790 C₂H₅ F F F CF₂CF₂ n-C₃H₇ 1791 C₂H₅ F F FCF₂CF₂ n-C₄H₉ 1792 C₂H₅ F F F CF₂CF₂ n-C₅H₁₁ 1793 C₂H₅ F F F CF₂CF₂n-C₆H₁₃ 1794 C₂H₅ F F F CF₂CF₂ n-C₇H₁₅ 1795 C₂H₅ F F F CF₂O CH₃ 1796C₂H₅ F F F CF₂O C₂H₅ 1797 C₂H₅ F F F CF₂O n-C₃H₇ 1798 C₂H₅ F F F CF₂On-C₄H₉ 1799 C₂H₅ F F F CF₂O n-C₅H₁₁ 1800 C₂H₅ F F F CF₂O n-C₆H₁₃ 1801C₂H₅ F F F CF₂O n-C₇H₁₅ 1802 C₂H₅ F F F Bond CH₃ 1803 C₂H₅ F F F BondC₂H₅ 1804 C₂H₅ F F F Bond n-C₃H₇ 1805 C₂H₅ F F F Bond n-C₄H₉ 1806 C₂H₅ FF F Bond n-C₅H₁₁ 1807 C₂H₅ F F F Bond n-C₆H₁₃ 1808 C₂H₅ F F F Bondn-C₇H₁₅ 1809 n-C₃H₇ F F F Bond CH₃ 1810 n-C₃H₇ F F F Bond C₂H₅ 1811n-C₃H₇ F F F Bond n-C₃H₇ 1812 n-C₃H₇ F F F Bond n-C₄H₉ 1813 n-C₃H₇ F F FBond n-C₅H₁₁ 1814 n-C₃H₇ F F F Bond n-C₆H₁₃ 1815 n-C₃H₇ F F F Bondn-C₇H₁₅ 1816 n-C₄H₉ F F F Bond CH₃ 1817 n-C₄H₉ F F F Bond C₂H₅ 1818n-C₄H₉ F F F Bond n-C₃H₇ 1819 n-C₄H₉ F F F Bond n-C₄H₉ 1820 n-C₄H₉ F F FBond n-C₅H₁₁ 1821 n-C₄H₉ F F F Bond n-C₆H₁₃ 1822 n-C₄H₉ F F F Bondn-C₇H₁₅ 1823 n-C₅H₁₁ F F F Bond CH₃ 1824 n-C₅H₁₁ F F F Bond C₂H₅ 1825n-C₅H₁₁ F F F Bond n-C₃H₇ 1826 n-C₅H₁₁ F F F Bond n-C₄H₉ 1827 n-C₅H₁₁ FF F Bond n-C₅H₁₁ 1828 n-C₅H₁₁ F F F Bond n-C₆H₁₃ 1829 n-C₅H₁₁ F F F Bondn-C₇H₁₅

Examples 1830-1871

Example E¹ X^(1a) X^(1b) X² X³ R 1830 H F F F F CH₃ 1831 H F F F F C₂H₅1832 H F F F F n-C₃H₇ 1833 H F F F F n-C₄H₉ 1834 H F F F F n-C₅H₁₁ 1835H F F F F n-C₆H₁₃ 1836 H F F F F n-C₇H₁₅ 1837 CH₃ F F F F CH₃ 1838 CH₃ FF F F C₂H₅ 1839 CH₃ F F F F n-C₃H₇ 1840 CH₃ F F F F n-C₄H₉ 1841 CH₃ F FF F n-C₅H₁₁ 1842 CH₃ F F F F n-C₆H₁₃ 1843 CH₃ F F F F n-C₇H₁₅ 1844 C₂H₅F F F F CH₃ 1845 C₂H₅ F F F F C₂H₅ 1846 C₂H₅ F F F F n-C₃H₇ 1847 C₂H₅ FF F F n-C₄H₉ 1848 C₂H₅ F F F F n-C₅H₁₁ 1849 C₂H₅ F F F F n-C₆H₁₃ 1850C₂H₅ F F F F n-C₇H₁₅ 1851 n-C₃H₇ F F F F CH₃ 1852 n-C₃H₇ F F F F C₂H₅1853 n-C₃H₇ F F F F n-C₃H₇ 1854 n-C₃H₇ F F F F n-C₄H₉ 1855 n-C₃H₇ F F FF n-C₅H₁₁ 1856 n-C₃H₇ F F F F n-C₆H₁₃ 1857 n-C₃H₇ F F F F n-C₇H₁₅ 1858n-C₄H₉ F F F F CH₃ 1859 n-C₄H₉ F F F F C₂H₅ 1860 n-C₄H₉ F F F F n-C₃H₇1861 n-C₄H₉ F F F F n-C₄H₉ 1862 n-C₄H₉ F F F F n-C₅H₁₁ 1863 n-C₄H₉ F F FF n-C₆H₁₃ 1864 n-C₄H₉ F F F F n-C₇H₁₅ 1865 n-C₅H₁₁ F F F F CH₃ 1866n-C₅H₁₁ F F F F C₂H₅ 1867 n-C₅H₁₁ F F F F n-C₃H₇ 1868 n-C₅H₁₁ F F F Fn-C₄H₉ 1869 n-C₅H₁₁ F F F F n-C₅H₁₁ 1870 n-C₅H₁₁ F F F F n-C₆H₁₃ 1871n-C₅H₁₁ F F F F n-C₇H₁₅

Example 1872-1941

Example E¹ X^(1a) X^(1b) X² X³ Z R 1872 H F F F F Bond CH₃ 1873 H F F FF Bond C₂H₅ 1874 H F F F F Bond n-C₃H₇ 1875 H F F F F Bond n-C₄H₉ 1876 HF F F F Bond n-C₅H₁₁ 1877 H F F F F Bond n-C₆H₁₃ 1878 H F F F F Bondn-C₇H₁₅ 1879 H F F F F CF₂CF₂ CH₃ 1880 H F F F F CF₂CF₂ C₂H₅ 1881 H F FF F CF₂CF₂ n-C₃H₇ 1882 H F F F F CF₂CF₂ n-C₄H₉ 1883 H F F F F CF₂CF₂n-C₅H₁₁ 1884 H F F F F CF₂CF₂ n-C₆H₁₃ 1885 H F F F F CF₂CF₂ n-C₇H₁₅ 1886H F F F F OCF₂ CH₃ 1887 H F F F F OCF₂ C₂H₅ 1888 H F F F F OCF₂ n-C₃H₇1889 H F F F F OCF₂ n-C₄H₉ 1890 H F F F F OCF₂ n-C₅H₁₁ 1891 H F F F FOCF₂ n-C₆H₁₃ 1892 H F F F F OCF₂ n-C₇H₁₅ 1893 CH₃ F F F F Bond CH₃ 1894CH₃ F F F F Bond C₂H₅ 1895 CH₃ F F F F Bond n-C₃H₇ 1896 CH₃ F F F F Bondn-C₄H₉ 1897 CH₃ F F F F Bond n-C₅H₁₁ 1898 CH₃ F F F F Bond n-C₆H₁₃ 1899CH₃ F F F F Bond n-C₇H₁₅ 1900 CH₃ F F F F CF₂CF₂ CH₃ 1901 CH₃ F F F FCF₂CF₂ C₂H₅ 1902 CH₃ F F F F CF₂CF₂ n-C₃H₇ 1903 CH₃ F F F F CF₂CF₂n-C₄H₉ 1904 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 1905 CH₃ F F F F CF₂CF₂ n-C₆H₁₃1906 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 1907 CH₃ F F F F OCF₂ CH₃ 1908 CH₃ F F FF OCF₂ C₂H₅ 1909 CH₃ F F F F OCF₂ n-C₃H₇ 1910 CH₃ F F F F OCF₂ n-C₄H₉1911 CH₃ F F F F OCF₂ n-C₅H₁₁ 1912 CH₃ F F F F OCF₂ n-C₆H₁₃ 1913 CH₃ F FF F OCF₂ n-C₇H₁₅ 1914 C₂H₅ F F F F Bond CH₃ 1915 C₂H₅ F F F F Bond C₂H₅1916 C₂H₅ F F F F Bond n-C₃H₇ 1917 C₂H₅ F F F F Bond n-C₄H₉ 1918 C₂H₅ FF F F Bond n-C₅H₁₁ 1919 C₂H₅ F F F F Bond n-C₆H₁₃ 1920 C₂H₅ F F F F Bondn-C₇H₁₅ 1921 n-C₃H₇ F F F F Bond CH₃ 1922 n-C₃H₇ F F F F Bond C₂H₅ 1923n-C₃H₇ F F F F Bond n-C₃H₇ 1924 n-C₃H₇ F F F F Bond n-C₄H₉ 1925 n-C₃H₇ FF F F Bond n-C₅H₁₁ 1926 n-C₃H₇ F F F F Bond n-C₆H₁₃ 1927 n-C₃H₇ F F F FBond n-C₇H₁₅ 1928 n-C₄H₉ F F F F Bond CH₃ 1929 n-C₄H₉ F F F F Bond C₂H₅1930 n-C₄H₉ F F F F Bond n-C₃H₇ 1931 n-C₄H₉ F F F F Bond n-C₄H₉ 1932n-C₄H₉ F F F F Bond n-C₅H₁₁ 1933 n-C₄H₉ F F F F Bond n-C₆H₁₃ 1934 n-C₄H₉F F F F Bond n-C₇H₁₅ 1935 n-C₅H₁₁ F F F F Bond CH₃ 1936 n-C₅H₁₁ F F F FBond C₂H₅ 1937 n-C₅H₁₁ F F F F Bond n-C₃H₇ 1938 n-C₅H₁₁ F F F F Bondn-C₄H₉ 1939 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 1940 n-C₅H₁₁ F F F F Bondn-C₆H₁₃ 1941 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 1942-2011

Example E¹ X^(1a) X^(1b) X² X³ Z R 1942 H F F F F Bond CH₃ 1943 H F F FF Bond C₂H₅ 1944 H F F F F Bond n-C₃H₇ 1945 H F F F F Bond n-C₄H₉ 1946 HF F F F Bond n-C₅H₁₁ 1947 H F F F F Bond n-C₆H₁₃ 1948 H F F F F Bondn-C₇H₁₅ 1949 H F F F F CF₂CF₂ CH₃ 1950 H F F F F CF₂CF₂ C₂H₅ 1951 H F FF F CF₂CF₂ n-C₃H₇ 1952 H F F F F CF₂CF₂ n-C₄H₉ 1953 H F F F F CF₂CF₂n-C₅H₁₁ 1954 H F F F F CF₂CF₂ n-C₆H₁₃ 1955 H F F F F CF₂CF₂ n-C₇H₁₅ 1956H F F F F CF₂O CH₃ 1957 H F F F F CF₂O C₂H₅ 1958 H F F F F CF₂O n-C₃H₇1959 H F F F F CF₂O n-C₄H₉ 1960 H F F F F CF₂O n-C₅H₁₁ 1961 H F F F FCF₂O n-C₆H₁₃ 1962 H F F F F CF₂O n-C₇H₁₅ 1963 CH₃ F F F F Bond CH₃ 1964CH₃ F F F F Bond C₂H₅ 1965 CH₃ F F F F Bond n-C₃H₇ 1966 CH₃ F F F F Bondn-C₄H₉ 1967 CH₃ F F F F Bond n-C₅H₁₁ 1968 CH₃ F F F F Bond n-C₆H₁₃ 1969CH₃ F F F F Bond n-C₇H₁₅ 1970 CH₃ F F F F CF₂CF₂ CH₃ 1971 CH₃ F F F FCF₂CF₂ C₂H₅ 1972 CH₃ F F F F CF₂CF₂ n-C₃H₇ 1973 CH₃ F F F F CF₂CF₂n-C₄H₉ 1974 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 1975 CH₃ F F F F CF₂CF₂ n-C₆H₁₃1976 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 1977 CH₃ F F F F CF₂O CH₃ 1978 CH₃ F F FF CF₂O C₂H₅ 1979 CH₃ F F F F CF₂O n-C₃H₇ 1980 CH₃ F F F F CF₂O n-C₄H₉1981 CH₃ F F F F CF₂O n-C₅H₁₁ 1982 CH₃ F F F F CF₂O n-C₆H₁₃ 1983 CH₃ F FF F CF₂O n-C₇H₁₅ 1984 C₂H₅ F F F F Bond CH₃ 1985 C₂H₅ F F F F Bond C₂H₅1986 C₂H₅ F F F F Bond n-C₃H₇ 1987 C₂H₅ F F F F Bond n-C₄H₉ 1988 C₂H₅ FF F F Bond n-C₅H₁₁ 1989 C₂H₅ F F F F Bond n-C₆H₁₃ 1990 C₂H₅ F F F F Bondn-C₇H₁₅ 1991 n-C₃H₇ F F F F Bond CH₃ 1992 n-C₃H₇ F F F F Bond C₂H₅ 1993n-C₃H₇ F F F F Bond n-C₃H₇ 1994 n-C₃H₇ F F F F Bond n-C₄H₉ 1995 n-C₃H₇ FF F F Bond n-C₅H₁₁ 1996 n-C₃H₇ F F F F Bond n-C₆H₁₃ 1997 n-C₃H₇ F F F FBond n-C₇H₁₅ 1998 n-C₄H₉ F F F F Bond CH₃ 1999 n-C₄H₉ F F F F Bond C₂H₅2000 n-C₄H₉ F F F F Bond n-C₃H₇ 2001 n-C₄H₉ F F F F Bond n-C₄H₉ 2002n-C₄H₉ F F F F Bond n-C₅H₁₁ 2003 n-C₄H₉ F F F F Bond n-C₆H₁₃ 2004 n-C₄H₉F F F F Bond n-C₇H₁₅ 2005 n-C₅H₁₁ F F F F Bond CH₃ 2006 n-C₅H₁₁ F F F FBond C₂H₅ 2007 n-C₅H₁₁ F F F F Bond n-C₃H₇ 2008 n-C₅H₁₁ F F F F Bondn-C₄H₉ 2009 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 2010 n-C₅H₁₁ F F F F Bondn-C₆H₁₃ 2011 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 2012-2081

Example E¹ X^(1a) X^(1b) X² X³ Z R 2012 H F F F F Bond CH₃ 2013 H F F FF Bond C₂H₅ 2014 H F F F F Bond n-C₃H₇ 2015 H F F F F Bond n-C₄H₉ 2016 HF F F F Bond n-C₅H₁₁ 2017 H F F F F Bond n-C₆H₁₃ 2018 H F F F F Bondn-C₇H₁₅ 2019 H F F F F CF₂CF₂ CH₃ 2020 H F F F F CF₂CF₂ C₂H₅ 2021 H F FF F CF₂CF₂ n-C₃H₇ 2022 H F F F F CF₂CF₂ n-C₄H₉ 2023 H F F F F CF₂CF₂n-C₅H₁₁ 2024 H F F F F CF₂CF₂ n-C₆H₁₃ 2025 H F F F F CF₂CF₂ n-C₇H₁₅ 2026H F F F F CF₂O CH₃ 2027 H F F F F CF₂O C₂H₅ 2028 H F F F F CF₂O n-C₃H₇2029 H F F F F CF₂O n-C₄H₉ 2030 H F F F F CF₂O n-C₅H₁₁ 2031 H F F F FCF₂O n-C₆H₁₃ 2032 H F F F F CF₂O n-C₇H₁₅ 2033 CH₃ F F F F Bond CH₃ 2034CH₃ F F F F Bond C₂H₅ 2035 CH₃ F F F F Bond n-C₃H₇ 2036 CH₃ F F F F Bondn-C₄H₉ 2037 CH₃ F F F F Bond n-C₅H₁₁ 2038 CH₃ F F F F Bond n-C₆H₁₃ 2039CH₃ F F F F Bond n-C₇H₁₅ 2040 CH₃ F F F F CF₂CF₂ CH₃ 2041 CH₃ F F F FCF₂CF₂ C₂H₅ 2042 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2043 CH₃ F F F F CF₂CF₂n-C₄H₉ 2044 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2045 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2046 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2047 CH₃ F F F F CF₂O CH₃ 2048 CH₃ F F FF CF₂O C₂H₅ 2049 CH₃ F F F F CF₂O n-C₃H₇ 2050 CH₃ F F F F CF₂O n-C₄H₉2051 CH₃ F F F F CF₂O n-C₅H₁₁ 2052 CH₃ F F F F CF₂O n-C₆H₁₃ 2053 CH₃ F FF F CF₂O n-C₇H₁₅ 2054 C₂H₅ F F F F Bond CH₃ 2055 C₂H₅ F F F F Bond C₂H₅2056 C₂H₅ F F F F Bond n-C₃H₇ 2057 C₂H₅ F F F F Bond n-C₄H₉ 2058 C₂H₅ FF F F Bond n-C₅H₁₁ 2059 C₂H₅ F F F F Bond n-C₆H₁₃ 2060 C₂H₅ F F F F Bondn-C₇H₁₅ 2061 n-C₃H₇ F F F F Bond CH₃ 2062 n-C₃H₇ F F F F Bond C₂H₅ 2063n-C₃H₇ F F F F Bond n-C₃H₇ 2064 n-C₃H₇ F F F F Bond n-C₄H₉ 2065 n-C₃H₇ FF F F Bond n-C₅H₁₁ 2066 n-C₃H₇ F F F F Bond n-C₆H₁₃ 2067 n-C₃H₇ F F F FBond n-C₇H₁₅ 2068 n-C₄H₉ F F F F Bond CH₃ 2069 n-C₄H₉ F F F F Bond C₂H₅2070 n-C₄H₉ F F F F Bond n-C₃H₇ 2071 n-C₄H₉ F F F F Bond n-C₄H₉ 2072n-C₄H₉ F F F F Bond n-C₅H₁₁ 2073 n-C₄H₉ F F F F Bond n-C₆H₁₃ 2074 n-C₄H₉F F F F Bond n-C₇H₁₅ 2075 n-C₅H₁₁ F F F F Bond CH₃ 2076 n-C₅H₁₁ F F F FBond C₂H₅ 2077 n-C₅H₁₁ F F F F Bond n-C₃H₇ 2078 n-C₅H₁₁ F F F F Bondn-C₄H₉ 2079 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 2080 n-C₅H₁₁ F F F F Bondn-C₆H₁₃ 2081 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 2082-2130

Example R^(b) X^(1a) X^(1b) X² X³ Z R^(a) 2082 CH₃ F F F F Bond CH₃ 2083CH₃ F F F F Bond C₂H₅ 2084 CH₃ F F F F Bond n-C₃H₇ 2085 CH₃ F F F F Bondn-C₄H₉ 2086 CH₃ F F F F Bond n-C₅H₁₁ 2087 CH₃ F F F F Bond n-C₆H₁₃ 2088CH₃ F F F F Bond n-C₇H₁₅ 2089 CH₃ F F F F CF₂CF₂ CH₃ 2090 CH₃ F F F FCF₂CF₂ C₂H₅ 2091 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2092 CH₃ F F F F CF₂CF₂n-C₄H₉ 2093 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2094 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2095 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2096 C₂H₅ F F F F CF₂CF₂ CH₃ 2097 C₂H₅ FF F F CF₂CF₂ C₂H₅ 2098 C₂H₅ F F F F CF₂CF₂ n-C₃H₇ 2099 C₂H₅ F F F FCF₂CF₂ n-C₄H₉ 2100 C₂H₅ F F F F CF₂CF₂ n-C₅H₁₁ 2101 C₂H₅ F F F F CF₂CF₂n-C₆H₁₃ 2102 C₂H₅ F F F F CF₂CF₂ n-C₇H₁₅ 2103 C₂H₅ F F F F Bond CH₃ 2104C₂H₅ F F F F Bond C₂H₅ 2105 C₂H₅ F F F F Bond n-C₃H₇ 2106 C₂H₅ F F F FBond n-C₄H₉ 2107 C₂H₅ F F F F Bond n-C₅H₁₁ 2108 C₂H₅ F F F F Bondn-C₆H₁₃ 2109 C₂H₅ F F F F Bond n-C₇H₁₅ 2110 n-C₃H₇ F F F F Bond CH₃ 2111n-C₃H₇ F F F F Bond C₂H₅ 2112 n-C₃H₇ F F F F Bond n-C₃H₇ 2113 n-C₃H₇ F FF F Bond n-C₄H₉ 2114 n-C₃H₇ F F F F Bond n-C₅H₁₁ 2115 n-C₃H₇ F F F FBond n-C₆H₁₃ 2116 n-C₃H₇ F F F F Bond n-C₇H₁₅ 2117 n-C₄H₉ F F F F BondCH₃ 2118 n-C₄H₉ F F F F Bond C₂H₅ 2119 n-C₄H₉ F F F F Bond n-C₃H₇ 2120n-C₄H₉ F F F F Bond n-C₄H₉ 2121 n-C₄H₉ F F F F Bond n-C₅H₁₁ 2122 n-C₄H₉F F F F Bond n-C₆H₁₃ 2123 n-C₄H₉ F F F F Bond n-C₇H₁₅ 2124 n-C₅H₁₁ F F FF Bond CH₃ 2125 n-C₅H₁₁ F F F F Bond C₂H₅ 2126 n-C₅H₁₁ F F F F Bondn-C₃H₇ 2127 n-C₅H₁₁ F F F F Bond n-C₄H₉ 2128 n-C₅H₁₁ F F F F Bondn-C₅H₁₁ 2129 n-C₅H₁₁ F F F F Bond n-C₆H₁₃ 2130 n-C₅H₁₁ F F F F Bondn-C₇H₁₅

Examples 2131-2193

Example R^(b) X^(1a) X^(1b) X² X³ Z R^(a) 2131 CH₃ F F F F Bond CH₃ 2132CH₃ F F F F Bond C₂H₅ 2133 CH₃ F F F F Bond n-C₃H₇ 2134 CH₃ F F F F Bondn-C₄H₉ 2135 CH₃ F F F F Bond n-C₅H₁₁ 2136 CH₃ F F F F Bond n-C₆H₁₃ 2137CH₃ F F F F Bond n-C₇H₁₅ 2138 CH₃ F F F F CF₂CF₂ CH₃ 2139 CH₃ F F F FCF₂CF₂ C₂H₅ 2140 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2141 CH₃ F F F F CF₂CF₂n-C₄H₉ 2142 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2143 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2144 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2145 CH₃ F F F F OCF₂ CH₃ 2146 CH₃ F F FF OCF₂ C₂H₅ 2147 CH₃ F F F F OCF₂ n-C₃H₇ 2148 CH₃ F F F F OCF₂ n-C₄H₉2149 CH₃ F F F F OCF₂ n-C₅H₁₁ 2150 CH₃ F F F F OCF₂ n-C₆H₁₃ 2151 CH₃ F FF F OCF₂ n-C₇H₁₅ 2152 C₂H₅ F F F F CF₂CF₂ CH₃ 2153 C₂H₅ F F F F CF₂CF₂C₂H₅ 2154 C₂H₅ F F F F CF₂CF₂ n-C₃H₇ 2155 C₂H₅ F F F F CF₂CF₂ n-C₄H₉2156 C₂H₅ F F F F CF₂CF₂ n-C₅H₁₁ 2157 C₂H₅ F F F F CF₂CF₂ n-C₆H₁₃ 2158C₂H₅ F F F F CF₂CF₂ n-C₇H₁₅ 2159 C₂H₅ F F F F OCF₂ CH₃ 2160 C₂H₅ F F F FOCF₂ C₂H₅ 2161 C₂H₅ F F F F OCF₂ n-C₃H₇ 2162 C₂H₅ F F F F OCF₂ n-C₄H₉2163 C₂H₅ F F F F OCF₂ n-C₅H₁₁ 2164 C₂H₅ F F F F OCF₂ n-C₆H₁₃ 2165 C₂H₅F F F F OCF₂ n-C₇H₁₅ 2166 C₂H₅ F F F F Bond CH₃ 2167 C₂H₅ F F F F BondC₂H₅ 2168 C₂H₅ F F F F Bond n-C₃H₇ 2169 C₂H₅ F F F F Bond n-C₄H₉ 2170C₂H₅ F F F F Bond n-C₅H₁₁ 2171 C₂H₅ F F F F Bond n-C₆H₁₃ 2172 C₂H₅ F F FF Bond n-C₇H₁₅ 2173 n-C₃H₇ F F F F Bond CH₃ 2174 n-C₃H₇ F F F F BondC₂H₅ 2175 n-C₃H₇ F F F F Bond n-C₃H₇ 2176 n-C₃H₇ F F F F Bond n-C₄H₉2177 n-C₃H₇ F F F F Bond n-C₅H₁₁ 2178 n-C₃H₇ F F F F Bond n-C₆H₁₃ 2179n-C₃H₇ F F F F Bond n-C₇H₁₅ 2180 n-C₄H₉ F F F F Bond CH₃ 2181 n-C₄H₉ F FF F Bond C₂H₅ 2182 n-C₄H₉ F F F F Bond n-C₃H₇ 2183 n-C₄H₉ F F F F Bondn-C₄H₉ 2184 n-C₄H₉ F F F F Bond n-C₅H₁₁ 2185 n-C₄H₉ F F F F Bond n-C₆H₁₃2186 n-C₄H₉ F F F F Bond n-C₇H₁₅ 2187 n-C₅H₁₁ F F F F Bond CH₃ 2188n-C₅H₁₁ F F F F Bond C₂H₅ 2189 n-C₅H₁₁ F F F F Bond n-C₃H₇ 2190 n-C₅H₁₁F F F F Bond n-C₄H₉ 2191 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 2192 n-C₅H₁₁ F F FF Bond n-C₆H₁₃ 2193 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 2194-2235

Example E¹ X^(1a) X^(1b) X² X³ R 2194 H F F F F CH₃ 2195 H F F F F C₂H₅2196 H F F F F n-C₃H₇ 2197 H F F F F n-C₄H₉ 2198 H F F F F n-C₅H₁₁ 2199H F F F F n-C₆H₁₃ 2200 H F F F F n-C₇H₁₅ 2201 CH₃ F F F F CH₃ 2202 CH₃ FF F F C₂H₅ 2203 CH₃ F F F F n-C₃H₇ 2204 CH₃ F F F F n-C₄H₉ 2205 CH₃ F FF F n-C₅H₁₁ 2206 CH₃ F F F F n-C₆H₁₃ 2207 CH₃ F F F F n-C₇H₁₅ 2208 C₂H₅F F F F CH₃ 2209 C₂H₅ F F F F C₂H₅ 2210 C₂H₅ F F F F n-C₃H₇ 2211 C₂H₅ FF F F n-C₄H₉ 2212 C₂H₅ F F F F n-C₅H₁₁ 2213 C₂H₅ F F F F n-C₆H₁₃ 2214C₂H₅ F F F F n-C₇H₁₅ 2215 n-C₃H₇ F F F F CH₃ 2216 n-C₃H₇ F F F F C₂H₅2217 n-C₃H₇ F F F F n-C₃H₇ 2218 n-C₃H₇ F F F F n-C₄H₉ 2219 n-C₃H₇ F F FF n-C₅H₁₁ 2220 n-C₃H₇ F F F F n-C₆H₁₃ 2221 n-C₃H₇ F F F F n-C₇H₁₅ 2222n-C₄H₉ F F F F CH₃ 2223 n-C₄H₉ F F F F C₂H₅ 2224 n-C₄H₉ F F F F n-C₃H₇2225 n-C₄H₉ F F F F n-C₄H₉ 2226 n-C₄H₉ F F F F n-C₅H₁₁ 2227 n-C₄H₉ F F FF n-C₆H₁₃ 2228 n-C₄H₉ F F F F n-C₇H₁₅ 2229 n-C₅H₁₁ F F F F CH₃ 2230n-C₅H₁₁ F F F F C₂H₅ 2231 n-C₅H₁₁ F F F F n-C₃H₇ 2232 n-C₅H₁₁ F F F Fn-C₄H₉ 2233 n-C₅H₁₁ F F F F n-C₅H₁₁ 2234 n-C₅H₁₁ F F F F n-C₆H₁₃ 2235n-C₅H₁₁ F F F F n-C₇H₁₅

Examples 2236-2305

Example E¹ X^(1a) X^(1b) X² X³ Z R 2236 H F F F F Bond CH₃ 2237 H F F FF Bond C₂H₅ 2238 H F F F F Bond n-C₃H₇ 2239 H F F F F Bond n-C₄H₉ 2240 HF F F F Bond n-C₅H₁₁ 2241 H F F F F Bond n-C₆H₁₃ 2242 H F F F F Bondn-C₇H₁₅ 2243 H F F F F CF₂CF₂ CH₃ 2244 H F F F F CF₂CF₂ C₂H₅ 2245 H F FF F CF₂CF₂ n-C₃H₇ 2246 H F F F F CF₂CF₂ n-C₄H₉ 2247 H F F F F CF₂CF₂n-C₅H₁₁ 2248 H F F F F CF₂CF₂ n-C₆H₁₃ 2249 H F F F F CF₂CF₂ n-C₇H₁₅ 2250H F F F F OCF₂ CH₃ 2251 H F F F F OCF₂ C₂H₅ 2252 H F F F F OCF₂ n-C₃H₇2253 H F F F F OCF₂ n-C₄H₉ 2254 H F F F F OCF₂ n-C₅H₁₁ 2255 H F F F FOCF₂ n-C₆H₁₃ 2256 H F F F F OCF₂ n-C₇H₁₅ 2257 CH₃ F F F F Bond CH₃ 2258CH₃ F F F F Bond C₂H₅ 2259 CH₃ F F F F Bond n-C₃H₇ 2260 CH₃ F F F F Bondn-C₄H₉ 2261 CH₃ F F F F Bond n-C₅H₁₁ 2262 CH₃ F F F F Bond n-C₆H₁₃ 2263CH₃ F F F F Bond n-C₇H₁₅ 2264 CH₃ F F F F CF₂CF₂ CH₃ 2265 CH₃ F F F FCF₂CF₂ C₂H₅ 2266 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2267 CH₃ F F F F CF₂CF₂n-C₄H₉ 2268 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2269 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2270 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2271 CH₃ F F F F OCF₂ CH₃ 2272 CH₃ F F FF OCF₂ C₂H₅ 2273 CH₃ F F F F OCF₂ n-C₃H₇ 2274 CH₃ F F F F OCF₂ n-C₄H₉2275 CH₃ F F F F OCF₂ n-C₅H₁₁ 2276 CH₃ F F F F OCF₂ n-C₆H₁₃ 2277 CH₃ F FF F OCF₂ n-C₇H₁₅ 2278 C₂H₅ F F F F Bond CH₃ 2279 C₂H₅ F F F F Bond C₂H₅2280 C₂H₅ F F F F Bond n-C₃H₇ 2281 C₂H₅ F F F F Bond n-C₄H₉ 2282 C₂H₅ FF F F Bond n-C₅H₁₁ 2283 C₂H₅ F F F F Bond n-C₆H₁₃ 2284 C₂H₅ F F F F Bondn-C₇H₁₅ 2285 n-C₃H₇ F F F F Bond CH₃ 2286 n-C₃H₇ F F F F Bond C₂H₅ 2287n-C₃H₇ F F F F Bond n-C₃H₇ 2288 n-C₃H₇ F F F F Bond n-C₄H₉ 2289 n-C₃H₇ FF F F Bond n-C₅H₁₁ 2290 n-C₃H₇ F F F F Bond n-C₆H₁₃ 2291 n-C₃H₇ F F F FBond n-C₇H₁₅ 2292 n-C₄H₉ F F F F Bond CH₃ 2293 n-C₄H₉ F F F F Bond C₂H₅2294 n-C₄H₉ F F F F Bond n-C₃H₇ 2295 n-C₄H₉ F F F F Bond n-C₄H₉ 2296n-C₄H₉ F F F F Bond n-C₅H₁₁ 2297 n-C₄H₉ F F F F Bond n-C₆H₁₃ 2298 n-C₄H₉F F F F Bond n-C₇H₁₅ 2299 n-C₅H₁₁ F F F F Bond CH₃ 2300 n-C₅H₁₁ F F F FBond C₂H₅ 2301 n-C₅H₁₁ F F F F Bond n-C₃H₇ 2302 n-C₅H₁₁ F F F F Bondn-C₄H₉ 2303 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 2304 n-C₅H₁₁ F F F F Bondn-C₆H₁₃ 2305 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 2306-2375

Example E¹ X^(1a) X^(1b) X² X³ Z R 2306 H F F F F Bond CH₃ 2307 H F F FF Bond C₂H₅ 2308 H F F F F Bond n-C₃H₇ 2309 H F F F F Bond n-C₄H₉ 2310 HF F F F Bond n-C₅H₁₁ 2311 H F F F F Bond n-C₆H₁₃ 2312 H F F F F Bondn-C₇H₁₅ 2313 H F F F F CF₂CF₂ CH₃ 2314 H F F F F CF₂CF₂ C₂H₅ 2315 H F FF F CF₂CF₂ n-C₃H₇ 2316 H F F F F CF₂CF₂ n-C₄H₉ 2317 H F F F F CF₂CF₂n-C₅H₁₁ 2318 H F F F F CF₂CF₂ n-C₆H₁₃ 2319 H F F F F CF₂CF₂ n-C₇H₁₅ 2320H F F F F CF₂O CH₃ 2321 H F F F F CF₂O C₂H₅ 2322 H F F F F CF₂O n-C₃H₇2323 H F F F F CF₂O n-C₄H₉ 2324 H F F F F CF₂O n-C₅H₁₁ 2325 H F F F FCF₂O n-C₆H₁₃ 2326 H F F F F CF₂O n-C₇H₁₅ 2327 CH₃ F F F F Bond CH₃ 2328CH₃ F F F F Bond C₂H₅ 2329 CH₃ F F F F Bond n-C₃H₇ 2330 CH₃ F F F F Bondn-C₄H₉ 2331 CH₃ F F F F Bond n-C₅H₁₁ 2332 CH₃ F F F F Bond n-C₆H₁₃ 2333CH₃ F F F F Bond n-C₇H₁₅ 2334 CH₃ F F F F CF₂CF₂ CH₃ 2335 CH₃ F F F FCF₂CF₂ C₂H₅ 2336 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2337 CH₃ F F F F CF₂CF₂n-C₄H₉ 2338 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2339 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2340 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2341 CH₃ F F F F CF₂O CH₃ 2342 CH₃ F F FF CF₂O C₂H₅ 2343 CH₃ F F F F CF₂O n-C₃H₇ 2344 CH₃ F F F F CF₂O n-C₄H₉2345 CH₃ F F F F CF₂O n-C₅H₁₁ 2346 CH₃ F F F F CF₂O n-C₆H₁₃ 2347 CH₃ F FF F CF₂O n-C₇H₁₅ 2348 C₂H₅ F F F F Bond CH₃ 2349 C₂H₅ F F F F Bond C₂H₅2350 C₂H₅ F F F F Bond n-C₃H₇ 2351 C₂H₅ F F F F Bond n-C₄H₉ 2352 C₂H₅ FF F F Bond n-C₅H₁₁ 2353 C₂H₅ F F F F Bond n-C₆H₁₃ 2354 C₂H₅ F F F F Bondn-C₇H₁₅ 2355 n-C₃H₇ F F F F Bond CH₃ 2356 n-C₃H₇ F F F F Bond C₂H₅ 2357n-C₃H₇ F F F F Bond n-C₃H₇ 2358 n-C₃H₇ F F F F Bond n-C₄H₉ 2359 n-C₃H₇ FF F F Bond n-C₅H₁₁ 2360 n-C₃H₇ F F F F Bond n-C₆H₁₃ 2361 n-C₃H₇ F F F FBond n-C₇H₁₅ 2362 n-C₄H₉ F F F F Bond CH₃ 2363 n-C₄H₉ F F F F Bond C₂H₅2364 n-C₄H₉ F F F F Bond n-C₃H₇ 2365 n-C₄H₉ F F F F Bond n-C₄H₉ 2366n-C₄H₉ F F F F Bond n-C₅H₁₁ 2367 n-C₄H₉ F F F F Bond n-C₆H₁₃ 2368 n-C₄H₉F F F F Bond n-C₇H₁₅ 2369 n-C₅H₁₁ F F F F Bond CH₃ 2370 n-C₅H₁₁ F F F FBond C₂H₅ 2371 n-C₅H₁₁ F F F F Bond n-C₃H₇ 2372 n-C₅H₁₁ F F F F Bondn-C₄H₉ 2373 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 2374 n-C₅H₁₁ F F F F Bondn-C₆H₁₃ 2375 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 2376-2445

Example E¹ X^(1a) X^(1b) X² X³ Z R 2376 H F F F F Bond CH₃ 2377 H F F FF Bond C₂H₅ 2378 H F F F F Bond n-C₃H₇ 2379 H F F F F Bond n-C₄H₉ 2380 HF F F F Bond n-C₅H₁₁ 2381 H F F F F Bond n-C₆H₁₃ 2382 H F F F F Bondn-C₇H₁₅ 2383 H F F F F CF₂CF₂ CH₃ 2384 H F F F F CF₂CF₂ C₂H₅ 2385 H F FF F CF₂CF₂ n-C₃H₇ 2386 H F F F F CF₂CF₂ n-C₄H₉ 2387 H F F F F CF₂CF₂n-C₅H₁₁ 2388 H F F F F CF₂CF₂ n-C₆H₁₃ 2389 H F F F F CF₂CF₂ n-C₇H₁₅ 2390H F F F F CF₂O CH₃ 2391 H F F F F CF₂O C₂H₅ 2392 H F F F F CF₂O n-C₃H₇2393 H F F F F CF₂O n-C₄H₉ 2394 H F F F F CF₂O n-C₅H₁₁ 2395 H F F F FCF₂O n-C₆H₁₃ 2396 H F F F F CF₂O n-C₇H₁₅ 2397 CH₃ F F F F Bond CH₃ 2398CH₃ F F F F Bond C₂H₅ 2399 CH₃ F F F F Bond n-C₃H₇ 2400 CH₃ F F F F Bondn-C₄H₉ 2401 CH₃ F F F F Bond n-C₅H₁₁ 2402 CH₃ F F F F Bond n-C₆H₁₃ 2403CH₃ F F F F Bond n-C₇H₁₅ 2404 CH₃ F F F F CF₂CF₂ CH₃ 2405 CH₃ F F F FCF₂CF₂ C₂H₅ 2406 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2407 CH₃ F F F F CF₂CF₂n-C₄H₉ 2408 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2409 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2410 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2411 CH₃ F F F F CF₂O CH₃ 2412 CH₃ F F FF CF₂O C₂H₅ 2413 CH₃ F F F F CF₂O n-C₃H₇ 2414 CH₃ F F F F CF₂O n-C₄H₉2415 CH₃ F F F F CF₂O n-C₅H₁₁ 2416 CH₃ F F F F CF₂O n-C₆H₁₃ 2417 CH₃ F FF F CF₂O n-C₇H₁₅ 2418 C₂H₅ F F F F Bond CH₃ 2419 C₂H₅ F F F F Bond C₂H₅2420 C₂H₅ F F F F Bond n-C₃H₇ 2421 C₂H₅ F F F F Bond n-C₄H₉ 2422 C₂H₅ FF F F Bond n-C₅H₁₁ 2423 C₂H₅ F F F F Bond n-C₆H₁₃ 2424 C₂H₅ F F F F Bondn-C₇H₁₅ 2425 n-C₃H₇ F F F F Bond CH₃ 2426 n-C₃H₇ F F F F Bond C₂H₅ 2427n-C₃H₇ F F F F Bond n-C₃H₇ 2428 n-C₃H₇ F F F F Bond n-C₄H₉ 2429 n-C₃H₇ FF F F Bond n-C₅H₁₁ 2430 n-C₃H₇ F F F F Bond n-C₆H₁₃ 2431 n-C₃H₇ F F F FBond n-C₇H₁₅ 2432 n-C₄H₉ F F F F Bond CH₃ 2433 n-C₄H₉ F F F F Bond C₂H₅2434 n-C₄H₉ F F F F Bond n-C₃H₇ 2435 n-C₄H₉ F F F F Bond n-C₄H₉ 2436n-C₄H₉ F F F F Bond n-C₅H₁₁ 2437 n-C₄H₉ F F F F Bond n-C₆H₁₃ 2438 n-C₄H₉F F F F Bond n-C₇H₁₅ 2439 n-C₅H₁₁ F F F F Bond CH₃ 2440 n-C₅H₁₁ F F F FBond C₂H₅ 2441 n-C₅H₁₁ F F F F Bond n-C₃H₇ 2442 n-C₅H₁₁ F F F F Bondn-C₄H₉ 2443 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 2444 n-C₅H₁₁ F F F F Bondn-C₆H₁₃ 2445 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

Examples 2446-2494

Example R^(b) X^(1a) X^(1b) X² X³ Z R^(a) 2446 CH₃ F F F F Bond CH₃ 2447CH₃ F F F F Bond C₂H₅ 2448 CH₃ F F F F Bond n-C₃H₇ 2449 CH₃ F F F F Bondn-C₄H₉ 2450 CH₃ F F F F Bond n-C₅H₁₁ 2451 CH₃ F F F F Bond n-C₆H₁₃ 2452CH₃ F F F F Bond n-C₇H₁₅ 2453 CH₃ F F F F CF₂CF₂ CH₃ 2454 CH₃ F F F FCF₂CF₂ C₂H₅ 2455 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2456 CH₃ F F F F CF₂CF₂n-C₄H₉ 2457 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2458 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2459 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2460 C₂H₅ F F F F CF₂CF₂ CH₃ 2461 C₂H₅ FF F F CF₂CF₂ C₂H₅ 2462 C₂H₅ F F F F CF₂CF₂ n-C₃H₇ 2463 C₂H₅ F F F FCF₂CF₂ n-C₄H₉ 2464 C₂H₅ F F F F CF₂CF₂ n-C₅H₁₁ 2465 C₂H₅ F F F F CF₂CF₂n-C₆H₁₃ 2466 C₂H₅ F F F F CF₂CF₂ n-C₇H₁₅ 2467 C₂H₅ F F F F Bond CH₃ 2468C₂H₅ F F F F Bond C₂H₅ 2469 C₂H₅ F F F F Bond n-C₃H₇ 2470 C₂H₅ F F F FBond n-C₄H₉ 2471 C₂H₅ F F F F Bond n-C₅H₁₁ 2472 C₂H₅ F F F F Bondn-C₆H₁₃ 2473 C₂H₅ F F F F Bond n-C₇H₁₅ 2474 n-C₃H₇ F F F F Bond CH₃ 2475n-C₃H₇ F F F F Bond C₂H₅ 2476 n-C₃H₇ F F F F Bond n-C₃H₇ 2477 n-C₃H₇ F FF F Bond n-C₄H₉ 2478 n-C₃H₇ F F F F Bond n-C₅H₁₁ 2479 n-C₃H₇ F F F FBond n-C₆H₁₃ 2480 n-C₃H₇ F F F F Bond n-C₇H₁₅ 2481 n-C₄H₉ F F F F BondCH₃ 2482 n-C₄H₉ F F F F Bond C₂H₅ 2483 n-C₄H₉ F F F F Bond n-C₃H₇ 2484n-C₄H₉ F F F F Bond n-C₄H₉ 2485 n-C₄H₉ F F F F Bond n-C₅H₁₁ 2486 n-C₄H₉F F F F Bond n-C₆H₁₃ 2487 n-C₄H₉ F F F F Bond n-C₇H₁₅ 2488 n-C₅H₁₁ F F FF Bond CH₃ 2489 n-C₅H₁₁ F F F F Bond C₂H₅ 2490 n-C₅H₁₁ F F F F Bondn-C₃H₇ 2491 n-C₅H₁₁ F F F F Bond n-C₄H₉ 2492 n-C₅H₁₁ F F F F Bondn-C₅H₁₁ 2493 n-C₅H₁₁ F F F F Bond n-C₆H₁₃ 2494 n-C₅H₁₁ F F F F Bondn-C₇H₁₅

Examples 2495-2557

Example R^(b) X^(1a) X^(1b) X² X³ Z R^(a) 2495 CH₃ F F F F Bond CH₃ 2496CH₃ F F F F Bond C₂H₅ 2497 CH₃ F F F F Bond n-C₃H₇ 2498 CH₃ F F F F Bondn-C₄H₉ 2499 CH₃ F F F F Bond n-C₅H₁₁ 2500 CH₃ F F F F Bond n-C₆H₁₃ 2501CH₃ F F F F Bond n-C₇H₁₅ 2502 CH₃ F F F F CF₂CF₂ CH₃ 2503 CH₃ F F F FCF₂CF₂ C₂H₅ 2504 CH₃ F F F F CF₂CF₂ n-C₃H₇ 2505 CH₃ F F F F CF₂CF₂n-C₄H₉ 2506 CH₃ F F F F CF₂CF₂ n-C₅H₁₁ 2507 CH₃ F F F F CF₂CF₂ n-C₆H₁₃2508 CH₃ F F F F CF₂CF₂ n-C₇H₁₅ 2509 CH₃ F F F F OCF₂ CH₃ 2510 CH₃ F F FF OCF₂ C₂H₅ 2511 CH₃ F F F F OCF₂ n-C₃H₇ 2512 CH₃ F F F F OCF₂ n-C₄H₉2513 CH₃ F F F F OCF₂ n-C₅H₁₁ 2514 CH₃ F F F F OCF₂ n-C₆H₁₃ 2515 CH₃ F FF F OCF₂ n-C₇H₁₅ 2516 C₂H₅ F F F F CF₂CF₂ CH₃ 2517 C₂H₅ F F F F CF₂CF₂C₂H₅ 2518 C₂H₅ F F F F CF₂CF₂ n-C₃H₇ 2519 C₂H₅ F F F F CF₂CF₂ n-C₄H₉2520 C₂H₅ F F F F CF₂CF₂ n-C₅H₁₁ 2521 C₂H₅ F F F F CF₂CF₂ n-C₆H₁₃ 2522C₂H₅ F F F F CF₂CF₂ n-C₇H₁₅ 2523 C₂H₅ F F F F OCF₂ CH₃ 2524 C₂H₅ F F F FOCF₂ C₂H₅ 2525 C₂H₅ F F F F OCF₂ n-C₃H₇ 2526 C₂H₅ F F F F OCF₂ n-C₄H₉2527 C₂H₅ F F F F OCF₂ n-C₅H₁₁ 2528 C₂H₅ F F F F OCF₂ n-C₆H₁₃ 2529 C₂H₅F F F F OCF₂ n-C₇H₁₅ 2530 C₂H₅ F F F F Bond CH₃ 2531 C₂H₅ F F F F BondC₂H₅ 2532 C₂H₅ F F F F Bond n-C₃H₇ 2533 C₂H₅ F F F F Bond n-C₄H₉ 2534C₂H₅ F F F F Bond n-C₅H₁₁ 2535 C₂H₅ F F F F Bond n-C₆H₁₃ 2536 C₂H₅ F F FF Bond n-C₇H₁₅ 2537 n-C₃H₇ F F F F Bond CH₃ 2538 n-C₃H₇ F F F F BondC₂H₅ 2539 n-C₃H₇ F F F F Bond n-C₃H₇ 2540 n-C₃H₇ F F F F Bond n-C₄H₉2541 n-C₃H₇ F F F F Bond n-C₅H₁₁ 2542 n-C₃H₇ F F F F Bond n-C₆H₁₃ 2543n-C₃H₇ F F F F Bond n-C₇H₁₅ 2544 n-C₄H₉ F F F F Bond CH₃ 2545 n-C₄H₉ F FF F Bond C₂H₅ 2546 n-C₄H₉ F F F F Bond n-C₃H₇ 2547 n-C₄H₉ F F F F Bondn-C₄H₉ 2548 n-C₄H₉ F F F F Bond n-C₅H₁₁ 2549 n-C₄H₉ F F F F Bond n-C₆H₁₃2550 n-C₄H₉ F F F F Bond n-C₇H₁₅ 2551 n-C₅H₁₁ F F F F Bond CH₃ 2552n-C₅H₁₁ F F F F Bond C₂H₅ 2553 n-C₅H₁₁ F F F F Bond n-C₃H₇ 2554 n-C₅H₁₁F F F F Bond n-C₄H₉ 2555 n-C₅H₁₁ F F F F Bond n-C₅H₁₁ 2556 n-C₅H₁₁ F F FF Bond n-C₆H₁₃ 2557 n-C₅H₁₁ F F F F Bond n-C₇H₁₅

TABLE 1 Δε- and Δn values for substances of individual examples ExampleNo. Δε Δn 10 −7.4 0.186 (Comp. 33) 80 −9.0 0.116 126 −8.4 0.100 154 −9.70.107 504 −8.5 0.124 2198 −10.7 0.067 2238 −6.0 0.070

1. A cyclopenta[a]naphthalene compound of formula I, II, Ill, IV or V

A is in each case, independently of one another, 1,4-phenylene, in which═CH— may be replaced once or twice by ═N—, and which may bemonosubstituted to tetrasubstituted, independently of one another, byhalogen (—F, —Cl, —Br, —I), —CN, —CH₃, —CH₂F, —CHF₂, —CF₃, —OCH₃,—OCH₂F, —OCHF₂ or —OCF₃, 1,4-cyclohexylene, 1,4-cyclohexenylene or1,4-cyclohexadienylene, in which —CH₂— may in each case be replaced onceor twice, independently of one another, by —O— or —S— in such a way thatheteroatoms are not linked directly, and which all may bemonosubstituted or polysubstituted by halogen; Z is in each case,independently of one another, a single bond, a double bond, —CF₂O—,—OCF₂—, —CH₂CH₂—, —CF₂CF₂—, —CF₂—CH₂—, —CH₂—CF₂—, —CHF—CHF—, —C(O)O—,—OC(O)—, —CH₂O—, —OCH₂—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH—or —C≡C—; Ris hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1to 15 or 2 to 15 carbon atoms respectively which is unsubstituted,monosubstituted by —CN or —CF₃ or at least monosubstituted by halogen,where, in addition, one or more CH₂ groups in these radicals may each,independently of one another, be replaced by —O—, —S—, —CO—, —COO—,—OCO—or —OCO—O— in such a way that heteroatoms are not linked directly,halogen, —CN, —SCN, —NCS, —SF₅, —CF₃, —OCF₃, —OCHF₂ or —OCH₂F; X¹,X^(1a), X^(1b), X² and X³ are each, independently of one another,hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to15 or 2 to 15 carbon atoms respectively which is unsubstituted or atleast monosubstituted by halogen, where, in addition, one or more CH₂groups in these radicals may each, independently of one another, bereplaced by —O—, —S—, —CO—, —COO—, —OCO—or —OCO—O—in such a way thatheteroatoms are not linked directly, halogen, —CN, —SF₅, —SCN, —NCS,—CF₃, —OCF₃, —OCHF₂ or —OCH₂F; E¹ and E² are each, independently of oneanother, hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical havingfrom 1 to 15 or 2 to 15 carbon atoms respectively which isunsubstituted, monosubstituted by —CN or —CF₃ or at leastmonosubstituted by halogen, where, in addition, one or more CH₂ groupsin these radicals may each, independently of one another, be replaced by—O—, —S—, —CO—, —COO—, —OCO—or —OCO—O— in such a way that heteroatomsare not linked directly, halogen, —CN, —SCN, —NCS, —SF₅, —CF₃, —OCF₃,—OCHF₂, —OCH₂F or —(—Z—A—)_(n)—R; and n is 1, 2 or 3; where in theformula I, ring B does not stand for the formula c if X¹, X² and X³ aresimultaneously hydrogen.
 2. A cyclopenta[a]naphthalene compoundaccording to claim 1, wherein


3. A cyclopenta[a]naphthalene compound according to claim 1, wherein Zis a single bond, —CF₂O—, —OCF₂—, —CF₂CF₂—, —CH═CH—, —CF═CH—, —CH═CF—or—CF═CF—.
 4. A cyclopenta[a]naphthalene compound according to claim 1,wherein A is


5. A cyclopenta[a]naphthalene compound according to claim 1, wherein Ris an alkyl radical, alkoxy radical or alkenyl radical having from 1 to7 or 2 to 7 carbon atoms respectively.
 6. A cyclopenta[a]naphthalenecompound according to claim 1, wherein E¹ and E², independently of oneanother, are hydrogen, an alkyl radical or alkoxy radical having from 1to 7 carbon atoms, fluorine, chlorine or —(-Z-A-)_(n)—R, in which n is1, Z is a single bond, A is 1,4-cyclohexylene or optionally mono- orpoly-fluorine-substituted 1,4-phenylene, and R is alkyl, alkoxy oralkenyl having from 1 to 7 or 2 to 7 carbon atoms respectively.
 7. Acyclopenta[a]naphthalene compound according to claim 1, wherein at leastone of X¹, X² and X³ or at least one of X^(1a), X^(1b), X³ and X³ is—CF₃, fluorine or chlorine.
 8. A cyclopenta[a]naphthalene compoundaccording to claim 1, wherein X¹, X² and X³ or X^(1a), X^(1b), X² and X³are —CF₃, fluorine and/or chlorine.
 9. A cyclopenta[a]naphthalenecompound according to claim 1, wherein X¹, X² and X³ or X^(1a), X^(1b),X² and X³ are fluorine.
 10. A liquid-crystalline medium comprising atleast two liquid-crystalline compounds, wherein at least oneliquid-crystalline compound is a cyclopenta[a]naphthalene compoundaccording to claim
 1. 11. An electro-optical display element containinga liquid-crystalline medium according to claim
 10. 12. Acyclopenta[a]naphthalene compound of formula VI, VII, VIII, IX or X,

A is in each case, independently of one another, 1,4-phenylene, in which═CH— may be replaced once or twice by ═N—, and which may bemonosubstituted to tetrasubstituted, independently of one another, byhalogen (—F, —Cl, —Br, —I), —CN, —CH₃, —CH₂F, —CHF₂, —CF₃, —OCH₃,—OCH₂F, —OCHF₂ or —OCF₃, 1,4-cyclohexylene, 1,4-cyclohexenylene or1,4-cyclohexadienylene, in which —CH₂— may in each case be replaced onceor twice, independently of one another, by —O— or —S— in such a way thatheteroatoms are not linked directly, and which all may bemonosubstituted or polysubstituted by halogen; Z is in each case,independently of one another, a single bond, a double bond, —CF₂O—,—OCF₂—, —CH₂CH₂—, —CF₂CF₂—, —CF₂—CH₂—, —CH₂—CF₂—, —CHF—CHF—, —C(O)O—,—OC(O)—, —CH₂O—, —OCH₂—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH—or C≡C—; R isan alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to15 carbon atoms respectively which is unsubstituted, monosubstituted by—CN or —CF₃ or at least monosubstituted by halogen, where, in addition,one or more CH₂ groups in these radicals may each, independently of oneanother, be replaced by —O—, —S—, —CO—, —COO—, —OCO—or —OCO—O—in such away that heteroatoms are not linked directly, halogen, —CN, —SCN, —NCS,—SF₅, —CF₃, —OCF₃, —OCHF₂or —OCH₂F; X¹, X^(1a), X^(1b), X² and X³ areeach, independently of one another, hydrogen, an alkyl, alkoxy, alkenylor alkynyl radical having from 1 to 15 or 2 to 15 carbon atomsrespectively which is unsubstituted or at least monosubstituted byhalogen, where, in addition, one or more CH₂ groups in these radicalsmay each, independently of one another, be replaced by —O—, —S—, —CO—,—COO—, —OCO—or —OCO—O—in such a way that heteroatoms are not linkeddirectly, halogen, —CN, —SF₅, —SCN, —NCS, —CF₃, —OCF₃, —OCHF₂ or —OCH₂F;E¹ and E² are each, independently of one another, hydrogen, an alkyl,alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbonatoms respectively which is unsubstituted, monosubstituted by —CN or—CF₃ or at least monosubstituted by halogen, where, in addition, one ormore CH₂ groups in these radicals may each, independently of oneanother, be replaced by —O—, —S—, —CO—, —COO—, —OCO—or —OCO—O—in such away that heteroatoms are not linked directly, halogen, —CN, —SCN, —NCS,—SF₅, —CF₃, —OCF₃, —OCHF₂, —OCH₂F or —(-Z-A-)_(n)—R; and n is 0, 1, 2 or3; where in formula VI, ring B does not stand for formula e if X² and X³are simultaneously fluorine or if E¹ is hydrogen and simultaneously X¹and X² are fluorine and at least one of X¹, X² and X³ or at least one ofX^(1a), X^(1b) and X² and X³ is —CF₃, fluorine and/or chlorine.
 13. Acyclopenta[a]naphthalene compound according to claim 12, wherein


14. A cyclopenta[a]naphthalene compound according to claim 12, wherein Zis a single bond, —CF₂O—, —OCF₂—, —CF₂CF₂—, —CH═CH—, —CF═CH—, —CH═CF—or—CF═CF—.
 15. A cyclopenta[a]naphthalene compound according to claim 12,wherein A is


16. A cyclopenta[a]naphthalene compound according to claim 12, wherein Ris an alkyl radical, alkoxy radical or alkenyl radical having from 1 to7 or 2 to 7 carbon atoms respectively.
 17. A cyclopenta[a]naphthalenecompound according to claim 1, wherein E¹ and E², independently of oneanother, are hydrogen, an alkyl radical or alkoxy radical having from 1to 7 carbon atoms, fluorine, chlorine or -(-Z-A-)_(n)—R, in which n is1, Z is a single bond, A is 1,4-cyclohexylene or optionally mono- orpoly-fluorine-substituted 1,4-phenylene, and R is alkyl, alkoxy oralkenyl having from 1 to 7 or 2 to 7 carbon atoms respectively.
 18. Aliquid-crystalline medium comprising at least two liquid-crystallinecompounds, wherein at least one liquid-crystalline compound is acyclopenta[a]naphthalene derivative according to claim
 12. 19. Anelectro-optical display element containing a liquid-crystalline mediumaccording to claim 18.